Formaldehyde → HCID 69033545, compound

HRID 351398Notes

Reaction equation

HRID 351398 reaction equation
[C:1]1([S:7]([CH2:10][C@@H:11]2[CH2:16][C@H:15]([NH:17][CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13][C@@H:12]2[N:21]2[CH2:26][CH2:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)=[CH:23][C:22]2=[O:37])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:40]([BH3-])#N.[Na+].O>CO>[C:1]1([S:7]([CH2:10][C@@H:11]2[CH2:16][C@H:15]([N:17]([CH:18]([CH3:20])[CH3:19])[CH3:40])[CH2:14][CH2:13][C@@H:12]2[N:21]2[CH2:26][CH2:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=3)=[CH:23][C:22]2=[O:37])(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 69035756HCID 69035756, compound

Product 1

HCID 69033545HCID 69033545, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-([(1S,2R,4R)-2-benzenesulfonylmethyl-4-isopropylamino-cyclohexyl)-4-(3-trifluoromethylphenyl)-5,6-dihydro-1H-pyridin-2-one (41 mg, 0.077 mmol) in methanol (1 mL) was treated with aqueous formaldehyde (37%, 0.029 mL, 0.383 mmol) and the mixture was stirred for 45 min. Sodium cyanoborohydride (7 mg, 0.115 mmol) was added, and the mixture stirred at room temperature for 2 h. Water was added and the mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate and concentrated under vacuum to provide the title product (42 mg) as a white glassy solid. MS found: (M+H)+=548.67.

Workup

  1. stirringthe mixture stirred at room temperature for 2 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-787ff2ee98c546a1aeb10abfdd59d459
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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