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

HRID 1695802노트

반응식

HRID 1695802 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:14]([Cl:17])=[N:15][CH:16]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2S(C1C=CC=CC=1)(=O)=O.N1C=CC=CC=1.[CH3:38][C:39]1[S:40][CH:41]=[C:42]([C:44](Cl)=[O:45])[N:43]=1>C(Cl)Cl>[Cl:17][C:14]1[N:15]=[CH:16][C:11]([C:9]2[CH:8]=[C:7]3[C:3]([CH:4]=[N:5][NH:6]3)=[C:2]([NH:1][C:44]([C:42]3[N:43]=[C:39]([CH3:38])[S:40][CH:41]=3)=[O:45])[CH:10]=2)=[CH:12][C:13]=1[NH:18][S:19]([CH3:22])(=[O:20])=[O:21]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 211839592-Methyl-1,3-thiazole-4-carbonyl chlorideHCID 58255829N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methanesulfonamide

생성물 1

HCID 44539723N-(6-{6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide수율 34.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methane sulfonamide (100 mg) was dissolved in DCM (5 ml) and pyridine (0.02 ml) was added. 2-Methyl-1,3-thiazole-4-carbonyl chloride (41 mg) was added and the reaction stirred at RT for 1 h. The reaction was evaporated to dryness and the residue was stirred in MeOH:2M NaOH (aq) (5 ml, 1:1, v/v) for 15 min. The reaction was neutralised with 2M HCl and evaporated to dryness. The residue was dissolved in DMSO (1 ml), filtered and purified by MDAP (method E). The pure fraction was evaporated to dryness to give title compound (33 mg).

후처리

  1. customThe reaction was evaporated to dryness
  2. stirringthe residue was stirred in MeOH
  3. wait2M NaOH (aq) (5 ml, 1:1, v/v) for 15 min
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in DMSO (1 ml)
  6. filtrationfiltered
  7. custompurified by MDAP (method E)
  8. customThe pure fraction was evaporated to dryness

출처 및 근거

ORD 기록
ord-8927739e4abb464e83142c1702d7d047
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163743B2

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