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Pyridine → N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-(chloromethyl)-1,3-thiazole-4-carboxamide

HRID 1695737
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인쇄 미리보기

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HRID 1695737 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH2:21])[C:5]2[CH:6]=[N:7][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1.N1C=CC=CC=1.[Cl:28][CH2:29][C:30]1[S:31][CH:32]=[C:33]([C:35](Cl)=[O:36])[N:34]=1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[C:4]([NH:21][C:35]([C:33]2[N:34]=[C:30]([CH2:29][Cl:28])[S:31][CH:32]=2)=[O:36])[CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 582557476-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amineHCID 597024562-(Chloromethyl)-1,3-thiazole-4-carbonyl chloride2회

생성물 1

HCID 58255773N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-(chloromethyl)-1,3-thiazole-4-carboxamide수율 86.6%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
3회

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온도
-10 °C

실험 절차

A three necked rounded bottomed flask was charged with 6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amine (12.7 g), anhydrous DCM (100 ml) and pyridine (7.5 ml) then placed under a nitrogen atmosphere and cooled to −10° C. A suspension of 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (9.39 g) in anhydrous DCM (75 ml) was added in one portion. The reaction mixture was stirred at room temperature for ˜4 hrs. Additional 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (1.36 g) in anhydrous DCM was added in one portion and the reaction was stirred overnight. The suspension was filtered, washing sparingly with DCM, then dried on the vacuum pump to give title compound (15.8 g).

후처리

  1. additionwas added in one portion
  2. stirringthe reaction was stirred overnight
  3. filtrationThe suspension was filtered
  4. washwashing sparingly with DCM
  5. customdried on the vacuum pump

출처 및 근거

ORD 기록
ord-22e62a23db4f441ca3b174e34677ea68
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163743B2

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