(2-Thienylmethyl)amine → HCID 71538600, compound

HRID 1519331Notes

Reaction equation

HRID 1519331 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].[S:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH2:38][NH2:39]>>[Cl:23][C:18]1[CH:17]=[C:16]([C:14]2[N:15]=[C:11]([C:9]3[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:31])[NH:39][CH2:38][C:34]5[S:33][CH:37]=[CH:36][CH:35]=5)=[CH:26][CH:25]=4)=[CH:7][CH:8]=3)[S:12][CH:13]=2)[CH:21]=[CH:20][C:19]=1[Cl:22]

Participants

3

Reactant 2

HCID 34005(2-Thienylmethyl)amineHCID 86679835HCID 86679835, compound2×

Product 1

HCID 71538600HCID 71538600, compoundYield 40%

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 2-thiophenemethylamine (available from Aldrich Chemical Company, Inc.; 70 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-4′-[(thiophen-2-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid (47 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.24 (br s, 1H), 9.24 (t, J=5.9 Hz, 1H), 8.48 (s, 1H), 8.36 (dd, J=16.8, 2.0 Hz, 2H), 8.24 (dd, J=8.0, 2.0 Hz, 1H), 8.10 (dd, J=8.4, 2.1 Hz, 1H), 7.94 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.3 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.40 (dd, J=5.1, 1.1 Hz, 1H), 7.04 (d, J=2.5 Hz, 1H), 6.98 (dd, J=5.0, 3.5 Hz, 1H), 4.67 (d, J=5.8 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-8145ac68229242a593ddf56ca3e2d425
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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