Benzylamine → HCID 71534958, compound

HRID 1519332Notes

Reaction equation

HRID 1519332 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:24]2[CH:29]=[CH:28][C:27]([C:30](O)=[O:31])=[CH:26][CH:25]=2)=[CH:7][CH:8]=[C:9]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[N:15]=2)[CH:10]=1)=[O:4].[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([NH:40][C:30]([C:27]1[CH:28]=[CH:29][C:24]([C:6]2[C:5]([C:3]([OH:2])=[O:4])=[CH:10][C:9]([C:11]3[S:12][CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=4)[N:15]=3)=[CH:8][CH:7]=2)=[CH:25][CH:26]=1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 86679835HCID 86679835, compound2×

Product 1

HCID 71534958HCID 71534958, compoundYield 64%

Procedure

Using the conditions of General Procedure E for Amide Coupling in Parallel Mode, 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 2-methyl ester (which may be prepared as described for Intermediate 8; 100 mg, 0.21 mmol) was reacted with benzylamine (available from Aldrich Chemical Company, Inc.; 66 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4′-benzylcarbamoyl-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (73 mg, 64%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.23 (br s, 1H), 9.15 (t, J=6.0 Hz, 1H), 8.48 (s, 1H), 8.39 (d, J=1.8 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.24 (dd, J=8.0, 1.8 Hz, 1H), 8.10 (dd, J=8.5, 2.0 Hz, 1H), 7.97 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.34 (d, J=4.3 Hz, 4H), 7.21-7.29 (m, 1H), 4.52 (d, J=6.0 Hz, 2H).

Workup

  1. customthe acid was purified
  2. customHPLC Purification Conditions B

Sources & evidence

ORD record
ord-d2a1c4103970486293efce57522e4913
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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