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

HRID 1695802ノート

反応式

HRID 1695802 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8927739e4abb464e83142c1702d7d047
出典データセット
uspto-grants-2012_04
特許番号
US08163743B2

反応ノート

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