Formaldehyde → HCID 178432908, compound

HRID 245750Notes

Reaction equation

HRID 245750 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][NH:19][CH3:20])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.C=O.[C:23]([BH3-])#N.[Na+]>C(O)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][N:19]([CH3:23])[CH3:20])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178484004HCID 178484004, compound

Product 1

HCID 178432908HCID 178432908, compoundYield 109.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred mixture of 1-((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)-N-methylmethanamine (0.148 mmol, 50 mg) and a 37% aqueous formaldehyde solution (0.445 mmol, 33.4 μL) was added sodium cyanoborohydride (0.163 mmol, 10.25 mg). After stirring for 30 minutes, acetic acid was added to adjust the pH of the reaction mixture to neutral. Stirring was continued for an additional hour during which time the pH was maintained neutral by addition of acetic acid. The reaction mixture was concentrated in vacuo. To the residue dichloromethane and 2N sodium hydroxide (aq) solution were added and the organic layer was separated. The aqueous layer was washed twice with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give 1-((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)-N,N-dimethylmethanamine (57 mg).

Workup

  1. stirringStirring
  2. waitwas continued for an additional hour during which time
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionTo the residue dichloromethane and 2N sodium hydroxide (aq) solution were added
  5. customthe organic layer was separated
  6. washThe aqueous layer was washed twice with dichloromethane
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5a5025049bf49aaad4bbb6653bfb90e
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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