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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
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HRID 79448 반응식
[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]
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참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 176
Acetic Acid
촉매
HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e986213dbc9b48e9b207312767d2eda2
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841455B2

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