Ethanol → 4-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid ethyl ester

HRID 661697Notes

Reaction equation

HRID 661697 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[CH:28]=[N:29][C:30]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:32]=2[C:33]#[N:34])=[CH:4][C:5]([C:15](=[O:26])[N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[CH3:17])=[C:6]([CH:14]=1)[O:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[CH2:39](O)[CH3:40]>O=S(Cl)Cl>[CH2:39]([O:12][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:14]=[C:2]([Cl:1])[C:3]([C:27]2[CH:28]=[N:29][C:30]([C:35]([F:38])([F:36])[F:37])=[CH:31][C:32]=2[C:33]#[N:34])=[CH:4][C:5]=1[C:15](=[O:26])[N:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[CH3:17])[CH3:40]

Participants

4

Reactant 2

HCID 702EthanolHCID 251589894-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid

Product 1

HCID 593703594-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideCatalyst

Procedure

To 4-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid in ethanol (1 mL), 10 drops of SOCl2 were added. The mixture was stirred at rt for 24 hrs. The crude was purified via reverse phase preparative LCMS to afford 4-{5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid ethyl ester 43-1 (12.2 mg). MS: [M+H]+ 576.3; tR=6.33 min (method 3).

Workup

  1. customThe crude was purified via reverse phase preparative LCMS

Sources & evidence

ORD record
ord-0e88085987b7434b96d073f346a9c799
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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