4-[5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester → 4-[5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid

HRID 661654Notes

Reaction equation

HRID 661654 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([C:18]2[CH:19]=[N:20][C:21]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:23]=2[C:24]#[N:25])=[CH:13][C:12]=1[C:30](=[O:40])[N:31]([CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[Cl:17][C:15]1[C:14]([C:18]2[CH:19]=[N:20][C:21]([C:26]([F:29])([F:27])[F:28])=[CH:22][C:23]=2[C:24]#[N:25])=[CH:13][C:12]([C:30](=[O:40])[N:31]([CH3:39])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])=[C:11]([CH:16]=1)[O:10][CH2:9][CH2:8][CH2:7][C:6]([OH:41])=[O:5]

Participants

4

Reactant 1

HCID 686031324-[5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester

Product 1

HCID 593703774-[5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acidYield 16.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-[5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester (410 mg, 0.7 mmol) was stirred in a mixture of trifluoroacetic acid in DCM (1/1, 3 mL) for 2 hrs. Concentration followed by purification by HPLC gave 4-[5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid 20-1 (62 mg). MS: 532.6 (M+H)+; tR=5.29 min (method 3). NMR (CDCl3, reported as the major isomer of cis-trans amide rotamers), 6, 8.54 (1H, s), 7.94 (1H, s), 7.34-7.25 (1H, m), 7.18-7.14 (2H, m), 7.14-7.04 (1H, m), 7.02 (1H, s), 6.92 (1H, s), 4.08 (2H, t, J=6.3 Hz), 3.40 (3H, s), 2.62 (2H, t, J=6.3 Hz), 2.30-2.18 (2H, m), 2.57 (3H, s).

Workup

  1. concentrationConcentration
  2. customfollowed by purification by HPLC

Sources & evidence

ORD record
ord-7bbaf6778bc94d67aa6c6eed77b9cd76
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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