Acetic Acid → HCID 86675142, compound

HRID 587681Notes

Reaction equation

HRID 587681 reaction equation
[Br:1][C:2]1[CH:16]=[C:15](/[CH:17]=[CH:18]/[CH:19]([C:24]2[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=2)[C:20]([F:23])([F:22])[F:21])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5].C=O.[CH3:35]C(O)=O.[BH3-]C#N.[Na+]>CO.CCOC(C)=O>[Br:1][C:2]1[CH:16]=[C:15](/[CH:17]=[CH:18]/[CH:19]([C:24]2[CH:25]=[C:26]([Cl:32])[C:27]([Cl:31])=[C:28]([Cl:30])[CH:29]=2)[C:20]([F:23])([F:21])[F:22])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][N:10]([CH3:35])[CH2:9][CH2:8]1)=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86675137HCID 86675137, compound

Product 1

HCID 86675142HCID 86675142, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-2-bromo-N-(piperidin-4-yl)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamide (0.1 g, 0.16 mmol), formaldehyde (30% in water) (0.1 mL, 0.16 mmol) and AcOH (0.01 mL) in MeOH (5.0 mL) was stirred at ambient temperature for 30 min. After that NaBH3CN (0.01 g, 0.16 mmol) was added at 0° C. and the reaction was stirred for 8 h at ambient temperature. The solvent was removed under reduced pressure to obtain residue which was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and brine solution. The combined EtOAc layer was dried over Na2SO4 and concentrated under reduced pressure to obtain a residue, which was triturated with Et2O/pentane to afford the title compound as a pale yellow gummy material (0.06 g, 59%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto obtain residue which
  3. washwashed with saturated aqueous NaHCO3 solution and brine solution
  4. dry with materialThe combined EtOAc layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a residue, which
  7. customwas triturated with Et2O/pentane

Sources & evidence

ORD record
ord-1647d538365043b4aee03193b11aa71e
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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