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Pyridine → N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-(chloromethyl)-1,3-thiazole-4-carboxamide

HRID 1695741
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HRID 1695741 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.N1C=CC=CC=1.[Cl:24][CH2:25][C:26]1[S:27][CH:28]=[C:29]([C:31](Cl)=[O:32])[N:30]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:17][C:31]([C:29]2[N:30]=[C:26]([CH2:25][Cl:24])[S:27][CH:28]=2)=[O:32])[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 582557836-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amineHCID 597024562-(Chloromethyl)-1,3-thiazole-4-carbonyl chloride

생성물 1

HCID 58255786N-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-(chloromethyl)-1,3-thiazole-4-carboxamide수율 67.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To 6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (1.47 g) in DCM (20 ml) was added pyridine (1 ml). The reaction mixture was stirred for 5 minutes at room temperature before 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (1.21 g) in DCM (20 ml) was added dropwise over 10 minutes. The reaction mixture was stirred at room temperature for 18 hours. Saturated sodium bicarbonate solution (40 ml) was added and the reaction was stirred vigorously before the organic layer was separated using a hydrophobic frit. The aqueous layer was extracted with further DCM and the combined organic layers were evaporated to dryness. The residual solid was dried on a high vacuum line before triturating with cyclohexane to give the title compound (1.52 g).

후처리

  1. additionwas added dropwise over 10 minutes
  2. stirringthe reaction was stirred vigorously before the organic layer
  3. customwas separated
  4. extractionThe aqueous layer was extracted with further DCM
  5. customthe combined organic layers were evaporated to dryness
  6. customThe residual solid was dried on a high vacuum line
  7. custombefore triturating with cyclohexane

출처 및 근거

ORD 기록
ord-da4ba152ae204accaca5ff5c985e463e
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163743B2

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