Hydrochloric Acid → HCID 59376466, compound

HRID 1694854Notes

Reaction equation

HRID 1694854 reaction equation
[NH:1]([C:8](=[O:47])[CH:9]([C:19]1[CH:46]=[CH:45][C:22]([C:23]([NH:25][C:26]2[C:30]([NH:31]C(=O)OC(C)(C)C)=[CH:29][N:28]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:27]=2)=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)(=O)C.CO.O1CCOCC1>[NH2:31][C:30]1[C:26]([NH:25][C:23]([C:22]2[CH:45]=[CH:46][C:19]([CH:9]([C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:11])[C:8]([NH:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:47])=[CH:20][CH:21]=2)=[O:24])=[N:27][N:28]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:29]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86642885HCID 86642885, compound

Product 1

HCID 59376466HCID 59376466, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl [3-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)-1-phenyl-1H-pyrazol-4-yl]carbamate (crude from above) in ethyl acetate (20 mL) and methanol (20 mL) was added 4M HCl in dioxane (10 mL) and the resulting solution was stirred at ambient temperature for 16 hours. The reaction was evaporated to dryness and purified by reverse phase LC to give 0.22 g (52%, 2 steps) of 2-(4-{[(4-amino-1-phenyl-1H-pyrazol-3-yl)amino]-carbonyl}phenyl)-N,N′-diphenyl-malonamide as a white solid. 1H NMR (600 MHz, CD3OD) δ 10.30 (s, 1H), 8.44 (s, 1H), 8.08 (d, J=8.5 Hz, 2H), 7.78 (d, J=8.8 Hz, 21-1), 7.74 (d, J=8.5 Hz, 2H), 7.58 (m, 4H), 7.51 (m, 2H), 7.36 (m, 1H), 7.32 (m, 4H), 7.11 (t, J=7.33 Hz, 2H); ESIMS calcd 531.2 (M++H), found 531.2 (M++H).

Workup

  1. customThe reaction was evaporated to dryness
  2. custompurified by reverse phase LC

Sources & evidence

ORD record
ord-24f289bd26ab4e068a02ff69d1fecd7a
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

Loading…