Acetic Acid → ethyl 3-(2-fluoro-4-{[4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzyl]amino}phenyl)propanoate

HRID 508053Notes

Reaction equation

HRID 508053 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[N:13]([CH2:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)[N:12]=[C:11]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:36]([F:47])[CH:35]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[F:47][C:36]1[CH:35]=[C:34]([NH:33][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([CH2:14][N:13]3[C:9]([CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:10][C:11]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=4)=[N:12]3)=[CH:16][CH:17]=2)[CH:39]=[CH:38][C:37]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231572154-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzaldehydeHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoate

Product 1

HCID 23157433ethyl 3-(2-fluoro-4-{[4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzyl]amino}phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzaldehyde (868 mg, 2.0 mmol), ethyl 3-(4-amino-2-fluorophenyl)propanoate (420 mg, 2.0 mmol), acetic acid (300 mg, 5.0 mmol) and 1,2-dichloroethane (15 mL) was added sodium triacetoxyborohydride (1.20 g, 6.0 mmol) by small portions at room temperature and the mixture was stirred for 1 hr. The reaction mixture was poured into 10% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane) to give the title compound as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e57dac89b437475fa56628058d104ea9
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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