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Water → N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamide

HRID 1695720
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HRID 1695720 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2.CCN(C(C)C)C(C)C.[CH3:27][CH:28]([N:30]1[C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=[N:31]1)[CH3:29].O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:17][C:35]([C:34]2[N:30]([CH:28]([CH3:29])[CH3:27])[N:31]=[CH:32][CH:33]=2)=[O:36])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2
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참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 582557836-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine2회HCID 583564221-Isopropyl-1H-pyrazole-5-carbonyl chloride

생성물 1

HCID 58255796N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamide수율 85.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (2.25 g, 7.59 mmol) was dissolved in DCM (40 ml) and DIPEA (2.85 ml, 16.34 mmol) was added. 1-(1-methylethyl)-1H-pyrazole-5-carbonyl chloride (1.41 g, 8.17 mmol) in DCM (10 ml) was added and the mixture left to stir at room temperature overnight. Water (50 ml) was added and the mixture vigorously stirred. The DCM layer was passed through a hydrophobic frit and evaporated to dryness. The material was combined with that obtained from a previous smaller scale reaction carried out in an identical manner but starting with 6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (0.2 g, 0.675 mmol). The combined crude materials were purified by chromatography on silica using a 50 g cartridge and eluting progressively with DCM, then 1-4% methanol in DCM. Product containing fractions were combined and evaporated to dryness to afford the title compound (2.8 g).

후처리

  1. waitthe mixture left
  2. stirringthe mixture vigorously stirred
  3. customevaporated to dryness
  4. customthat obtained from a previous smaller scale reaction
  5. customwere purified by chromatography on silica using a 50 g cartridge
  6. washeluting progressively with DCM
  7. additionProduct containing fractions
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-dc4b1e30e7284d57a735f0213be4e9af
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163743B2

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