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

HRID 1486010Notes

Reaction equation

HRID 1486010 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-26cc42e0f9664eb3b5ed55a1f10402de
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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