Ammonia → 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxamide

HRID 1396410Notes

Reaction equation

HRID 1396410 reaction equation
[NH3:1].CO.[N:4]1[N:5]([C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[C:20]([Cl:22])[N:19]=[N:18][C:17]=3[C:23]([O:25]CC)=O)[CH:12]=[CH:11][CH:10]=2)[N:6]=[CH:7][CH:8]=1>>[N:6]1[N:5]([C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[C:20]([Cl:22])[N:19]=[N:18][C:17]=3[C:23]([NH2:1])=[O:25])[CH:12]=[CH:11][CH:10]=2)[N:4]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689760ethyl 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylate

Product 1

HCID 866897614-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxamideYield 98%

Conditions

Temperature
35 °C

Procedure

Ammonia in methanol (3.94 g, 5 mL, 35.0 mmol) was added to ethyl 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (100 mg, 289 μmol) and stirred at 35° C. for 16 h. The mixture was concentrated in vacuo to give 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxamide (90 mg, 284 μmol, 98%) as an off-white solid. 1H NMR (400 MHz, DMSO-d) δ ppm 12.30 (s, 1H), 9.13 (s, 1H), 9.54 (s, 1H), 8.94 (s, 1H), 8.29 (s, 1H), 8.27 (s, 2H), 8.05 (t, J=8.1 Hz, 1H), 7.72 (d, J=7.9 Hz, 1H), 7.23 (d, J=8.1 Hz, 1H); MS (EI/CI) m/z: 316.9 [M+H].

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-cda2b48b84414209a152f316acddadde
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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