Formaldehyde → HCID 178432908、化合物

HRID 245750ノート

反応式

HRID 245750 の反応式
[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

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178484004HCID 178484004、化合物

生成物 1

HCID 178432908HCID 178432908、化合物収率 109.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d5a5025049bf49aaad4bbb6653bfb90e
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

反応ノート

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