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1-Methylpiperazine → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79448
ノート
印刷プレビュー

反応式

HRID 79448 の反応式
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([CH2:24][CH:25]=O)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[N:4]=1)[CH3:2].[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([CH2:24][CH2:25][N:39]4[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[N:4]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86672219N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 67259922N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
触媒
HCID 6344Dichloromethane溶媒

実験手順

The crude N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide (112 mg, 0.248 mmol), and N-methylpiperazine (25 mg, 0.25 mmol) were dissolved in DCM (5 mL), and treated with 10 equivalents of sodium triacetoxyborohydride, followed by 2 drops of glacial acetic acid. The reaction mixture was stirred at ambient temperature for 48 hours. The reaction mixture was concentrated, and resuspended in saturated aqueous sodium carbonate. The mixture was extracted with DCM and EtOAc, the combined organic layers were dried over anhydrous sodium sulfate, then filtered and concentrated. Purification of the crude material by preparative thin-layer chromatography on silica with 7N NH3-MeOH/MeOH/DCM, 2/8/98 as eluent afforded 83.5 mg of a foamy, white solid. MS (ES+APCI) m/z=537 (M+H) detected.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe mixture was extracted with DCM and EtOAc
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the crude material by preparative thin-layer chromatography on silica with 7N NH3-MeOH/MeOH/DCM, 2/8/98 as eluent
  7. customafforded 83.5 mg of a foamy, white solid

出典と根拠

ORDレコード
ord-e986213dbc9b48e9b207312767d2eda2
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841455B2

反応ノート

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