3-(3-(2-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-ylcarbamoyl)-4-(piperidin-1-yl)phenylcarbamoyl)-benzylthio)propanoic acid → 3-((3-((4-(Piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)carbamoyl)benzyl)thio)propanoic acid

HRID 2409846Notes

Reaction equation

HRID 2409846 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:26]([O-])=O)=[C:6]([CH:25]=1)[C:7]([NH:9][C:10]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[N:11]=1)=[O:8].CC1C=C(N2C=CC(NC(C3C=C(N4CCCCC4)C=CC=3N[C:58]([C:60]3[CH:61]=[C:62]([CH:70]=[CH:71][CH:72]=3)[CH2:63][S:64][CH2:65][CH2:66][C:67]([OH:69])=[O:68])=[O:59])=O)=N2)C=CC=1C.ClC1C=CC([N+]([O-])=O)=C(C=1)C(NC1C=C[N:84]([C:87]2[CH:92]=[CH:91][C:90]([CH3:93])=C(C)C=2)N=1)=O>>[N:84]1([C:2]2[CH:3]=[CH:4][C:5]([NH:26][C:58]([C:60]3[CH:61]=[C:62]([CH:70]=[CH:71][CH:72]=3)[CH2:63][S:64][CH2:65][CH2:66][C:67]([OH:69])=[O:68])=[O:59])=[C:6]([C:7](=[O:8])[NH:9][C:10]3[CH:14]=[CH:13][N:12]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=4)[N:11]=3)[CH:25]=2)[CH2:87][CH2:92][CH2:91][CH2:90][CH2:93]1

Participants

4

Reactant 3

HCID 566437253-(3-(2-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-ylcarbamoyl)-4-(piperidin-1-yl)phenylcarbamoyl)-benzylthio)propanoic acidHCID 665874355-chloro-2-nitro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamideHCID 665874615-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitrobenzamide

Product 1

HCID 565953303-((3-((4-(Piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)carbamoyl)benzyl)thio)propanoic acid

Procedure

This compound was prepared from 5-chloro-2-nitro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamide 6c using the procedure described for the preparation of 3-(3-(2-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-ylcarbamoyl)-4-(piperidin-1-yl)phenylcarbamoyl)-benzylthio)propanoic acid 5 from 5-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitrobenzamide 4g. 1H-NMR (300 MHz, CD3OD, ppm): δ 8.715 (d, J=6.9 Hz, 1H), 8.390-8.397 (m, 1H), 8.180 (s, 1H), 8.057-8.077 (m, 1H), 8.020 (s, 2H), 7.894-7.914 (m, 1H), 7.679-7.719 (m, 2H), 7.591-7.642 (m, 2H), 7.520-7.558 (m, 1H), 7.147-7.154 (m, 1H), 3.889 (s, 2H), 3.614-3.640 (m, 4H), 2.690-2.725 (m, 2H), 2.563-2.598 (m, 2H), 2.002-2.055 (m, 4H), 1.804-1.818 (m, 2H). MS (ES, m/z): 652 [M+H]+.

Sources & evidence

ORD record
ord-417352616cde46f9a7ac9024835ba26c
Source dataset
uspto-grants-2014_08
Patent number
US08815910B2

Reaction notes

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