Formaldehyde → HCID 178432908, 화합물

HRID 245750노트

반응식

HRID 245750 반응식
[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

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178484004HCID 178484004, 화합물

생성물 1

HCID 178432908HCID 178432908, 화합물수율 109.6%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d5a5025049bf49aaad4bbb6653bfb90e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

반응 노트

불러오는 중…