(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamine → 3-(3-(4-(Piperidin-1-yl)-2-(4-(1-(3-(trifluoromethyl)phenyl)ethylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)propanoic acid

HRID 1408153Notes

Reaction equation

HRID 1408153 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][CH:46]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[NH:28][C:29]([C:31]2[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=2)[CH2:34][S:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:30])[CH:11]=1)=[O:9].F[C:50](F)(F)C1C=C(C(N)C)C=CC=1>>[N:22]1([C:20]2[CH:19]=[CH:18][C:17]([NH:28][C:29]([C:31]3[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=3)[CH2:34][S:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:30])=[C:16]([C:12]3[CH:11]=[C:10]([C:8](=[O:9])[NH:7][CH:6]([C:5]4[CH:44]=[CH:45][CH:46]=[C:3]([C:2]([F:47])([F:1])[F:48])[CH:4]=4)[CH3:50])[CH:15]=[CH:14][N:13]=3)[CH:21]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 2782448(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamineHCID 566494063-(3-((2-(4-((3-(Trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoic acid

Product 1

HCID 665880523-(3-(4-(Piperidin-1-yl)-2-(4-(1-(3-(trifluoromethyl)phenyl)ethylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)propanoic acid

Procedure

This compound was prepared using the procedure used to prepare 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)-benzylthio)propanoic acid 1.1, using 1-(3-(trifluoromethyl)phenyl)ethanamine in place of 3-(trifluoromethyl)benzylamine. 1H-NMR (300 MHz, CD3OD, ppm): δ 9.044-9.062 (d, J=5.4 Hz, 1H), 8.786-8.816 (d, J=9.0 Hz, 1H), 8.378 (s, 1H), 8.125-8.133 (d, J=2.4 Hz, 1H), 8.003 (s, 1H), 7.875-7.905 (m, 2H), 7.707-7.754 (m, 3H), 7.499-7.623 (m, 4H), 5.324-5.393 (m, 1H), 3.913 (s, 2H), 3.678-3.714 (m, 4H), 2.709-2.754 (m, 2H), 2.574-2.618 (m, 2H), 2.043-2.060 (m, 4H), 1.831-1.846 (m, 2H), 1.641-1.664 (d, j=6.9 Hz, 3H). MS (ES, m/z): 692 [M+H]+.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-f9ad0dde293a4c698762a4d05953d566
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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