Formaldehyde → HCID 68458276, compound

HRID 2356844Notes

Reaction equation

HRID 2356844 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH:11]([C:13](=[O:36])[NH:14][C:15]1[N:16]([C:32]([CH3:35])([CH3:34])[CH3:33])[N:17]=[C:18]([C:20]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[CH3:40]C([O-])=O.[Na+].[BH3-]C#N.[Na+]>CO>[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH:11]([C:13](=[O:36])[NH:14][C:15]1[N:16]([C:32]([CH3:33])([CH3:35])[CH3:34])[N:17]=[C:18]([C:20]2([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:25][CH2:24][N:23]([CH3:40])[CH2:22][CH2:21]2)[CH:19]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68456693HCID 68456693, compound

Product 1

HCID 68458276HCID 68458276, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.67 g (1.3 mmol) of {1-[2-tert-butyl-5-(4-phenylpiperidin-4-yl)-2H-pyrazol-3-ylcarbamoyl]ethyl}carbamic acid benzyl ester, 0.33 mL (4.0 mmol) of 37% aq. formaldehyde, 0.33 g (4.0 mmol) of NaOAc and 0.27 g (4.3 mmol) of NaCNBH3 in 10 mL of MeOH was stirred at rt. After 16 h, the reaction mixture was concentrated and extracted with water and EtOAc. The organic layer was dried over MgSO4, and concentrated. Purification on silica gel using 4% Et3N-MeOH as eluant afforded {1-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-ylcarbamoyl]ethyl}carbamic acid benzyl ester.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with water and EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customPurification on silica gel using 4% Et3N-MeOH as eluant

Sources & evidence

ORD record
ord-6d7022eddd364654aaab0babd8cc00e7
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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