Acetaldehyde → HCID 16066188, compound

HRID 1171610Notes

Reaction equation

HRID 1171610 reaction equation
[CH:1]([NH:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([N:11]2[CH2:16][CH2:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[CH:13][C:12]2=[O:27])[C@H:7]([CH2:28][S:29]([CH:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[CH2:6]1)([CH3:3])[CH3:2].[CH:35](=O)[CH3:36].C([BH3-])#N.[Na+]>CO>[CH:1]([N:4]([CH2:35][CH3:36])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:16][CH2:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=3)=[CH:13][C:12]2=[O:27])[C@H:7]([CH2:28][S:29]([CH:32]([CH3:34])[CH3:33])(=[O:30])=[O:31])[CH2:6]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68769449HCID 68769449, compound

Product 1

HCID 16066188HCID 16066188, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[(1R,2R,4S)-4-isopropylamino-2-(propane-2-sulfonylmethyl)cyclohexyl]-4-(3-trifluoromethyl-phenyl)-5,6-dihydro-1H-pyridin-2-one (43 mg) in methanol (1 mL) was treated with acetaldehyde (0.025 mL) and stirred at room temperature. After 35 min, sodium cyanoborohydride (8 mg) was added, and the mixture was stirred at room temperature for 22.5 h. The mixture was concentrated and partitioned between water and ethyl acetate. The aqueous phase was extracted with additional ethyl acetate, and the combined organic phases were dried over sodium sulfate and concentrated under vacuum to provide 1-((1S,2R,4R)-4-(isopropyl(ethyl)amino)-2-(isopropylsulfonylmethyl)cyclohexyl)-4-(3-(trifluoromethyl)phenyl)-5,6-dihydropyridin-2(1H)-one (41 mg) as a white glassy solid. MS found: (M+H)+=529.39.

Workup

  1. stirringthe mixture was stirred at room temperature for 22.5 h
  2. concentrationThe mixture was concentrated
  3. custompartitioned between water and ethyl acetate
  4. extractionThe aqueous phase was extracted with additional ethyl acetate
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-08f9c78d84f74249ac2859f697eecff6
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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