Acetic Acid → HCID 10162183、化合物

HRID 8277ノート

反応式

HRID 8277 の反応式
N[CH2:2][C:3]([NH:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[N:22][N:21]4[CH2:31][CH2:32][CH2:33][C:20]=34)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:5])[CH3:4].[C:34]([BH3-])#[N:35].[Na+].[C:38](O)(=O)C.C=O>CO>[CH3:38][N:35]([CH3:34])[CH2:2][C:3]([NH:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[N:22][N:21]4[CH2:31][CH2:32][CH2:33][C:20]=34)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:5])[CH3:4]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 219926594-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid(2-amino-1,1-dimethyl-ethyl)-amide

生成物 1

HCID 10162183HCID 10162183、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

A mixture of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid(2-amino-1,1-dimethyl-ethyl)-amide (0.12 g, 0.27 mmol), sodium cyanoborohydride (0.038 g, 0.6 mmol), and acetic acid (0.077 mL, 1.3 mmol) in methanol (5 mL) is cooled to 0° C. and stirred for 10 min. A solution of 37% aqueous formaldehyde (0.086 mL, 3.1 mmol) in methanol (2 mL) is added dropwise. The mixture is allowed to warm to room temperature and stirred for 1 h. The reaction is quenched with saturated aqueous potassium carbonate solution and concentrated in vacuo. The residue is taken up in chloroform, washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue is chromatographed on SiO2 (8% methanol/92% dichloromethane) to yield the title compound, 33 mg (27%), as a white foam.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 h
  3. customThe reaction is quenched with saturated aqueous potassium carbonate solution
  4. concentrationconcentrated in vacuo
  5. washwashed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on SiO2 (8% methanol/92% dichloromethane)

出典と根拠

ORDレコード
ord-299b9a551a6048d98adae389038ab081
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

反応ノート

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