Hydrochloric Acid → HCID 58976335, compound

HRID 1179251Notes

Reaction equation

HRID 1179251 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([NH:12][C:13]2[N:17]=[C:16]([NH2:18])[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:14]=2)[CH:5]=1.C1COCC1.[OH-].[Na+].Cl>O.CO>[NH2:18][C:16]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:14]=[C:13]([NH:12][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[O:10][CH3:11])[C:3]([OH:25])=[O:2])[N:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58976227HCID 58976227, compound

Product 1

HCID 58976335HCID 58976335, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 3-(5-Amino-1-pyridin-2-yl-1H-[1,2,4]triazol-3-ylamino)-4-methoxy-benzoic acid methyl ester (1.31 g, 3.85 mmol) in a mixed solvent of THF (40 mL), MeOH (5 mL) and water (10 mL) was treated with 2N NaOH (8 mL) at 50° C. for 1 h. The reaction mixture was cooled to room temperature, neutralized with 6N HCl. Precipitate came out and collected by filtration to give the title compound (1.20 g) in 95% yield. Small amount was further purified by HPLC. FIA-MS: m/e=327.1 (M+H), 325.0 (M−H). Rt=3.09 min (Method A). 1H-NMR (500 MHz, DMSO(d6)): 12.53 (s, 1H), 8.81 (d, 1H), 8.43 (dd, 1H), 8.01 (td, 1H), 7.78 (s, 2H), 7.65 (d, 1H), 7.56 (s, 1H), 7.353 (dd, 1H), 7.23 (dd, 1H), 7.07 (dd, 1H), 3.92 (s, 3H).

Workup

  1. filtrationcollected by filtration

Sources & evidence

ORD record
ord-dbb288b1c8f947fea7d5704c729b871a
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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