1-Phenethylamine → HCID 71534961, compound

HRID 1519333Notes

Reaction equation

HRID 1519333 reaction equation
C[O:2][C:3]([C:5]1[C:6](C2C=CC(C(O)=O)=CC=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].[CH3:33][CH:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH: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:8]4[CH:7]=[CH:6][C:5]([C:3](=[O:2])[NH:41][CH:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH3:33])=[CH:10][CH:9]=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 74081-PhenethylamineHCID 86679835HCID 86679835, compound2×

Product 1

HCID 71534961HCID 71534961, compoundYield 114.6%

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 DL-alpha-methylbenzylamine (available from Aldrich Chemical Company, Inc.; 75 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′-(1-phenyl-ethylcarbamoyl)-biphenyl-2-carboxylic acid (69 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.22 (br s, 1H), 8.90 (d, J=8.0 Hz, 1H), 8.48 (s, 1H), 8.38 (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), 7.96 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.3 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.49 (d, J=8.3 Hz, 2H), 7.39-7.45 (m, 2H), 7.34 (t, J=7.7 Hz, 2H), 7.18-7.28 (m, 1H), 5.20 (quin, J=7.3 Hz, 1H), 1.50 (d, J=7.0 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-16b3588883d9481db80fdbde2ea07955
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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