Ammonia → HCID 58976008, compound

HRID 1179252Notes

Reaction equation

HRID 1179252 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:17](O)=[O:18])[N:3]=1.C1COCC1.C(N1C=CN=C1)([N:32]1C=CN=C1)=O.N>CO.O.CN(C=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:17]([NH2:32])=[O:18])[N:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 58976335HCID 58976335, compound

Product 1

HCID 58976008HCID 58976008, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-(5-Amino-1-pyridin-2-yl-1H-[1,2,4]triazol-3-ylamino)-4-methoxy-benzoic acid (108 mg, 0.8 mmol) in a mixed solvent of THF (50 mL) and DMF (15 mL) was treated with 1,1′-carbonyldiimidazole (194 mg, 1.2 mmol) at room temperature. After 1 h, ammonia in MeOH (7.0M, 1 mL) was added. The reaction mixture was stirred at 50 C for 16 h, poured into water. Precipitate was collected by filtration and further purified by HPLC to give 3-(5-Amino-1-pyridin-2-yl-1H-[1,2,4]triazol-3-ylamino)-4-methoxy-benzamide (112 mg). FIA-MS: m/e=326.1 (M+1). Rt=2.65 min (Method A). 1H-NMR(500 MHz, DMSO(d6): 8.65 (d, 1H), 8.43 (dd, 1H), 8.02 (td, 1H), 7.98 (m, 1H), 7.83 (m, 1H), 7.73 (d, 1H), 7.70 (m, 1H), 7.47 (dd, 1H), 7.27 (ff, 1H), 7.14 (m, 1H), 7.04 (d, 1H), 3.90 (s, 1H).

Workup

  1. filtrationPrecipitate was collected by filtration
  2. customfurther purified by HPLC

Sources & evidence

ORD record
ord-4032a48429814cae8495262a713046d2
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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