1,2-Dichloro-3-isocyanatobenzene → 1-(1-(3-(3-amino-2-methyl-3-oxopropyl)phenyl)-3-(2-fluorophenyl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea

HRID 1696593Notes

Reaction equation

HRID 1696593 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:13][CH:14]([CH3:18])[C:15]([NH2:17])=[O:16])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH:3]=1.[Cl:26][C:27]1[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=1[N:34]=[C:35]=[O:36]>>[NH2:17][C:15](=[O:16])[CH:14]([CH3:18])[CH2:13][C:9]1[CH:8]=[C:7]([N:6]2[C:2]([NH:1][C:35]([NH:34][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:27]=3[Cl:26])=[O:36])=[CH:3][C:4]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[N:5]2)[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 67270420HCID 67270420, compound

Product 1

HCID 117063621-(1-(3-(3-amino-2-methyl-3-oxopropyl)phenyl)-3-(2-fluorophenyl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)ureaYield 18%

Procedure

Using general method A, 3-(3-(5-amino-3-(2-fluorophenyl)-1H-pyrazol-1-yl)phenyl)-2-methylpropanamide (0.1225 g, 0.362 mmol, 1.00 eq) was combined with 2,3-dichlorophenyl isocyanate (0.102 g, 0.543 mmol, 1.50 eq) to yield 34.2 mg (18%) of pure 1-(1-(3-(3-amino-2-methyl-3-oxopropyl)phenyl)-3-(2-fluorophenyl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea. 1H NMR (DMSO-d6): δ 9.40 (s, 1H), 8.89 (s, 1H), 8.11-8.08 (s, 1H), 8.02-7.98 (m, 1H), 7.53-7.39 (m, 4H), 7.36-7.26 (m, 6H), 6.92-6.91 (m, 1H), 6.76 (brs, 1H), 3.00-2.93 (m, 1H), 2.65-2.57 (m, 2H), 1.03-1.02 (m, 3H); MS (ESI) m/z: 526.0 (M+H), 528.0 (M+2+H+).

Sources & evidence

ORD record
ord-2f81f51798f049d09ca4be79d7371006
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…