Ammonia → SB-431542

HRID 991544Notes

Reaction equation

HRID 991544 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([C:22]4[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=4)[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][C:5]=2[O:4][CH2:3]1.[NH3:31]>O1CCCC1>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH2:31])=[O:27])=[CH:24][CH:23]=4)[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22394525HCID 22394525, compound

Product 1

HCID 4521392SB-431542Yield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzoyl chloride hydrochloride (100 mg; 0.23 mmol) was suspended in tetrahydrofuran (5 ml) and treated with 0.88 aq. ammonia solution (1 ml) and the resulting mixture stirred at ambient temperature. The title compound (42 mg; 48%) was obtained as a brown powder and collected by filtration, washed with water and dried at 40° C. under reduced pressure. 1H NMR (250 MHz, CDCl3) δ: 5.50-6.40 (2H, br, exchangeable), 6.03 (2H, s), 6.90 (1H, d, J=8 Hz), 7.15 (3H, m), 7.55 (2H, brm), 7.89 (2H, d, J=8 Hz), 8.06 (2H, d, J=8 Hz), 8.54 (1H, brd); (ESMS) (M+H)+=385.4.

Sources & evidence

ORD record
ord-bac4aa1ee401418d976efb1f628b2eb2
Source dataset
uspto-grants-2002_10
Patent number
US06465493B1

Reaction notes

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