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Diisopropylethylamine → 5-Chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2-methyl-4-o-tolyl-thiazol-5-yl)-amide

HRID 474355
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반응식

HRID 474355 반응식
[CH3:1][C:2]1[S:3][C:4]([NH2:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:6]=1.C(N(C(C)C)CC)(C)C.[Cl:24][C:25]1[N:30]=[CH:29][N:28]2[N:31]=[CH:32][C:33]([C:34](Cl)=[O:35])=[C:27]2[CH:26]=1>ClCCl>[CH3:1][C:2]1[S:3][C:4]([NH:14][C:34]([C:33]2[CH:32]=[N:31][N:28]3[CH:27]=[CH:26][C:25]([Cl:24])=[N:30][C:29]=23)=[O:35])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:6]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 580630422-Methyl-4-o-tolyl-thiazol-5-ylamineHCID 866614395-Chloropyrazolo[1,5-c]pyrimidine-3-carbonyl chloride

생성물 1

HCID 580633685-Chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2-methyl-4-o-tolyl-thiazol-5-yl)-amide수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매
2회

실험 절차

To an ice-cooled solution of 2-methyl-4-o-tolyl-thiazol-5-ylamine (55.0 mg, 0.27 mmol, 1.0 equiv) and diisopropylethylamine (52.0 mg, 0.41 mmol, 1.5 equiv) in dichloromethane (10 mL) was added a solution of 5-chloropyrazolo[1,5-c]pyrimidine-3-carbonyl chloride (58.0 mg, 0.27 mmol, 1.0 equiv) in dichloromethane (5 mL). The reaction mixture was warmed to ambient temperature and stirred overnight. The mixture was washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under vacuum. Purification by flash column chromatography on silica gel (gradient: 0 to 3% methanol in dichloromethane) afforded 74.0 mg (73%) of 5-chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2-methyl-4-o-tolyl-thiazol-5-yl)-amide as a solid. LCMS (ESI) m+H=384.0 (mono chlorinated isotope pattern); 1H NMR (400 MHz, CDCl3) δ: 9.73 (s, 1H), 8.70 (s, 1H), 8.63 (d, 1H), 7.44-7.30 (m, 4H), 6.93 (d, 1H), 2.72 (s, 3H), 2.31 (s, 3H).

후처리

  1. washThe mixture was washed with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification by flash column chromatography on silica gel (gradient: 0 to 3% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-dea8d64fc3ec4a7a8041ef02d013a218
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637526B2

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