4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate in N,N-dimethyl-formamide

1.1: 88 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl / CH2Cl2 2.1: 83 percent / Bu3P / CH2Cl2 / 72 h / 20 °C 3.1: 98 percent / trifluoroacetic acid / CH2Cl2; H2O / 20 °C 4.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 5.1: H2 / Pd/C / tetrahydrofuran; methanol 6.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 6.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 7.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: 99 percent / LiOH / tetrahydrofuran; H2O / 20 °C 2.1: 88 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl / CH2Cl2 3.1: 83 percent / Bu3P / CH2Cl2 / 72 h / 20 °C 4.1: 98 percent / trifluoroacetic acid / CH2Cl2; H2O / 20 °C 5.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 6.1: H2 / Pd/C / tetrahydrofuran; methanol 7.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 7.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 8.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: 61 percent / p-toluenesulfonic acid / 60 °C 2.1: 100 percent / LiOH / tetrahydrofuran; H2O / 20 - 40 °C 3.1: 83 percent / Bu3P / CH2Cl2 / 72 h / 20 °C 4.1: 98 percent / trifluoroacetic acid / CH2Cl2; H2O / 20 °C 5.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 6.1: H2 / Pd/C / tetrahydrofuran; methanol 7.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 7.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 8.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 2.1: H2 / Pd/C / tetrahydrofuran; methanol 3.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 3.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 4.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: H2 / Pd/C / tetrahydrofuran; methanol 2.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 2.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 3.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: 83 percent / Bu3P / CH2Cl2 / 72 h / 20 °C 2.1: 98 percent / trifluoroacetic acid / CH2Cl2; H2O / 20 °C 3.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 4.1: H2 / Pd/C / tetrahydrofuran; methanol 5.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 5.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 6.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: 83 percent / Bu3P / CH2Cl2 / 72 h / 20 °C 2.1: 98 percent / trifluoroacetic acid / CH2Cl2; H2O / 20 °C 3.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 4.1: H2 / Pd/C / tetrahydrofuran; methanol 5.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 5.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 6.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: 100 percent / LiOH / tetrahydrofuran; H2O / 20 - 40 °C 2.1: 83 percent / Bu3P / CH2Cl2 / 72 h / 20 °C 3.1: 98 percent / trifluoroacetic acid / CH2Cl2; H2O / 20 °C 4.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 5.1: H2 / Pd/C / tetrahydrofuran; methanol 6.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 6.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 7.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme

1.1: 98 percent / trifluoroacetic acid / CH2Cl2; H2O / 20 °C 2.1: 49 percent / diethyl azodicarboxylate; PPh3 / CH2Cl2 / 20 °C 3.1: H2 / Pd/C / tetrahydrofuran; methanol 4.1: aniline; NaNO2; NaOAc / aq. HCl; methanol; tetrahydrofuran 4.2: Na2S2O4; NaOAc / ethanol; H2O; tetrahydrofuran 5.1: 85 percent / HATU; 4-methylmorpholine / dimethylformamide View Scheme