Aniline → HCID 21905231, compound

HRID 1247428Notes

Reaction equation

HRID 1247428 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([CH:21]=O)[C:15]=2[F:23])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[BH4-].[Na+]>CCO>[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([CH2:21][NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:15]=2[F:23])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6115AnilineHCID 4311764Sodium borohydrideHCID 21905731HCID 21905731, compound

Product 1

HCID 21905231HCID 21905231, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-formyl-phenyl)-2-ethoxy-acetamide (250 mg, example 311.3) in EtOH (5 ml) was added aniline (64 mg). The suspension was stirred over night, then cooled to 0° C. and treated with NaBH4 (38 mg). The reaction mixture was stirred 1 h at 0° and 1 h at rt, then poured onto ice and extracted with EtOAc. The organic layer was dried over MgSO4, filtrated and concentrated. The crude product was purified by flash chromatography (cyclohexane/EtOAc 1:4=>EtOAc) to give (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-phenylaminomethyl-phenyl)-2-ethoxy-acetamide (230 mg) as off-white amourphous solid. MS 436.3 ([M+H]+)

Workup

  1. stirringThe reaction mixture was stirred 1 h at 0° and 1 h at rt
  2. additionpoured onto ice
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (cyclohexane/EtOAc 1:4=>EtOAc)

Sources & evidence

ORD record
ord-fe0255cba61d4062a30061559d329b04
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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