4-Pyridinemethanamine → HCID 71537774, compound

HRID 1519325Notes

Reaction equation

HRID 1519325 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].[NH2:33][CH2:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1>>[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:2])=[O:4])[C:6]([C:24]4[CH:25]=[CH:26][C:27]([C:30](=[O:31])[NH:33][CH2:34][C:35]5[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=5)=[CH:28][CH:29]=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 773174-PyridinemethanamineHCID 86679835HCID 86679835, compound2×

Product 1

HCID 71537774HCID 71537774, compoundYield 68%

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 4-(aminomethyl)pyridine (available from Aldrich Chemical Company, Inc.; 67 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′-[(pyridin-4-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid (78 mg, 68%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.16 (br s, 1H), 9.25 (t, J=5.8 Hz, 1H), 8.60 (d, J=6.0 Hz, 2H), 8.47 (s, 1H), 8.40 (d, J=1.8 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.25 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.3, 2.0 Hz, 1H), 7.99 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.3 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 7.46-7.55 (m, 4H), 4.60 (d, J=5.8 Hz, 7H).

Workup

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

Sources & evidence

ORD record
ord-f2621375fe044ec09b99cd1b40b1425a
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

Loading…