(1R,2R)-2-{[4-(3-fluoro-4-{[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino}phenyl)phenyl]carbonyl}cyclopentane-1-carboxylic acid → (1R,2R)-2-({4'-[(5-methyl-1,3-benzoxazol-2-yl)amino]-1,1'-biphenyl-4-yl}carbonyl)cyclopentanecarboxylic acid

HRID 9616Notes

Reaction equation

HRID 9616 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.FC1C=C([C:41]2[CH:46]=[CH:45][C:44]([C:47]([C@@H:49]3[CH2:53][CH2:52][CH2:51][C@H:50]3[C:54]([OH:56])=[O:55])=[O:48])=[CH:43][CH:42]=2)C=CC=1NC1SC2C=C(OC(F)(F)F)C=CC=2N=1>>[CH3:18][C:15]1[CH:16]=[CH:17][C:11]2[O:10][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([C:41]4[CH:42]=[CH:43][C:44]([C:47]([C@@H:49]5[CH2:53][CH2:52][CH2:51][C@H:50]5[C:54]([OH:56])=[O:55])=[O:48])=[CH:45][CH:46]=4)=[CH:3][CH:4]=3)=[N:13][C:12]=2[CH:14]=1

Participants

3

Reactant 2

HCID 11444140(1R,2R)-2-{[4-(3-fluoro-4-{[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino}phenyl)phenyl]carbonyl}cyclopentane-1-carboxylic acidHCID 21985825N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amine

Product 1

HCID 11385144(1R,2R)-2-({4'-[(5-methyl-1,3-benzoxazol-2-yl)amino]-1,1'-biphenyl-4-yl}carbonyl)cyclopentanecarboxylic acidYield 17%

Procedure

This compound was prepared from N-(4-bromophenyl)-N-(5-methyl-1,3-benzoxazol-2-yl)amine (0.50 g, 1.65 mmol), methyl (1R,2R)-2-(4-bromobenzoyl) cyclopentanecarboxylate (0.57 g, 1.83 mmol, 94.5% ee) in a similar manner to the method described for (1R,2R)-2-({3′-fluoro-4′-[(6-trifluoromethoxy-1,3-benzothiazol-2-yl)amino]-1,1′-biphenyl-4-yl}carbonyl)cyclopentanecarboxylic acid. Yield: 17%. 1H NMR (400 MHz, DMSO-d6) δ 10.80 (s, 1 H), 8.05 (d, 2 H), 7.75–7.90 (m, 6 H), 7.35 (d, 1 H), 7.25 (s, 1 H), 6.95 (d, 1 H), 4.05 (q, 1 H), 3.20 (s, 1 H), 2.40 (s, 3 H), 2.15 (m, 1 H), 2.00 (m, 1 H), 1.55–1.80 (m, 4 H). LC-MS m/z 441.3 (MH+), ret. time 3.48 min.

Sources & evidence

ORD record
ord-b17c21f2f46f4fe0a90d984846a7e30c
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Reaction notes

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