Ethyl 3-(5-(2-formyl-3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate → Ethyl 3-(5-(2-(hydroxymethyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405259Notes

Reaction equation

HRID 405259 reaction equation
[CH:1]([C:3]1[C:8]([C:9]([CH3:11])=[CH2:10])=[CH:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][C:4]=1[C:16]1[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:23])=[N:20][CH:21]=1)=[O:2]>C1COCC1.CO>[OH:2][CH2:1][C:3]1[C:8]([CH:9]([CH3:11])[CH3:10])=[CH:7][C:6]([C:12]([F:14])([F:13])[F:15])=[CH:5][C:4]=1[C:16]1[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:23])=[N:20][CH:21]=1

Participants

4

Reactant 1

HCID 86674290Ethyl 3-(5-(2-formyl-3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 71059694Ethyl 3-(5-(2-(hydroxymethyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(5-(2-formyl-3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate (150.1 mg, 0.35 mmol) in THF (5 mL) and MeOH (25 mL) was hydrogenated substituting H-Cube (10 Bar H2) at 40° C. at a flow rate of 1 mL/min. The resulting solution was concentrated to yield the title compound.

Workup

  1. customat 40° C.
  2. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-016e727f47f344399746509c69635178
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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