Pyridine → 2-(Chloromethyl)-N-[6-{6-(methyloxy)-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 1695724노트

반응식

HRID 1695724 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:14]([O:17][CH3:18])=[N:15][CH:16]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25].N1C=CC=CC=1.[Cl:39][CH2:40][C:41]1[S:42][CH:43]=[C:44]([C:46](Cl)=[O:47])[N:45]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:39][CH2:40][C:41]1[S:42][CH:43]=[C:44]([C:46]([NH:1][C:2]2[CH:10]=[C:9]([C:11]3[CH:16]=[N:15][C:14]([O:17][CH3:18])=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:12]=3)[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][N:6]3[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[O:47])[N:45]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 597024562-(Chloromethyl)-1,3-thiazole-4-carbonyl chlorideHCID 66911247N-[5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide

생성물 1

HCID 582557402-(Chloromethyl)-N-[6-{6-(methyloxy)-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide수율 74.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

N-[5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide (700 mg, 1.478 mmol) was dissolved in DCM (30 ml) and cooled to 0° C. before pyridine (0.179 ml, 2.217 mmol) was added. To this mixture was added 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (290 mg, 1.478 mmol) as a solution in DCM (10 ml) dropwise over 15 mins. The mixture was stirred at 0° C. for 30 min. Saturated aqueous sodium bicarbonate solution (20 ml) was added to the mixture and it was stirred vigorously for 10 mins. The organic layer was separated using a hydrophobic frit, washed with water (20 ml) and concentrated in vacuo to give the title compound as an orange solid (697 mg).

후처리

  1. additionwas added
  2. stirringwas stirred vigorously for 10 mins
  3. customThe organic layer was separated
  4. washwashed with water (20 ml)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-25d41b9840934539bf364cc6e8d7e7a9
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163743B2

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