(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 907756Notes

Reaction equation

HRID 907756 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.Br[C:20]1[CH:36]=[CH:35][C:23]([C:24]([C@@H:26]2[CH2:30][CH2:29][CH2:28][C@H:27]2[C:31]([O:33]C)=[O:32])=[O:25])=[CH:22][CH:21]=1.FC1C=C(C2C=CC(C([C@@H]3CCC[C@H]3C(O)=O)=O)=CC=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:20]4[CH:21]=[CH:22][C:23]([C:24]([C@@H:26]5[CH2:30][CH2:29][CH2:28][C@H:27]5[C:31]([OH:33])=[O:32])=[O:25])=[CH:35][CH:36]=4)=[CH:3][CH:4]=3)=[N:13][C:12]=2[CH:14]=1

Participants

4

Reactant 3

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-amineHCID 58681296(1R,2R)-Methyl 2-(4-bromobenzoyl)cyclopentanecarboxylate

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, 1H), 8.05 (d, 2H), 7.75-7.90 (m, 6H), 7.35 (d, 1H), 7.25 (s, 1H), 6.95 (d, 1H), 4.05 (q, 1H), 3.20 (s, 1H), 2.40 (s, 3H), 2.15 (m, 1H), 2.00 (m, 1H), 1.55-1.80 (m, 4H). LC-MS m/z 441.3 (MH+), ret. time 3.48 min.

Sources & evidence

ORD record
ord-83966dbf57314adf8b0c1edb9a9c91a8
Source dataset
uspto-grants-2011_09
Patent number
US08013166B2

Reaction notes

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