3-Methylthietan-3-amine → 5-chloro-6-{[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carbonyl]-amino}-1H-indazole-7-carboxylic acid (3-methyl-thietan-3-yl)-amide

HRID 245632ノート

反応式

HRID 245632 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:29]=[N:28][NH:27][C:5]2=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[N:13]([C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=3)[N:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[O:8][C:7]2=[O:26].[CH3:30][C:31]1([NH2:35])[CH2:34][S:33][CH2:32]1>CN(C)C=O>[CH3:30][C:31]1([NH:35][C:7]([C:6]2[C:11]([NH:10][C:9]([C:12]3[N:13]([C:19]4[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=4)[N:14]=[C:15]([O:17][CH3:18])[CH:16]=3)=[O:8])=[C:2]([Cl:1])[CH:3]=[C:4]3[C:5]=2[NH:27][N:28]=[CH:29]3)=[O:26])[CH2:34][S:33][CH2:32]1

参加物

4

反応物 2

HCID 552816773-Methylthietan-3-amineHCID 579901685-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

生成物 1

HCID 579901485-chloro-6-{[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carbonyl]-amino}-1H-indazole-7-carboxylic acid (3-methyl-thietan-3-yl)-amide収率 44.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 500 mg (1.16 mmol) of the above 5-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one in 10 mL of N,N-dimethylformamide is added 396 mg (3.49 mmol) of 3-methyl-thietan-3-ylamine. The reaction is stirred at 60° C. for 72 hours and then concentrated in vacuo. The residue is taken-up with water and ethyl acetate. The phases are separated and the aqueous layer is washed three times with ethyl acetate. The combined organic layers are washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography (SiO2, hexanes/ethyl acetate 1:2) affords 276 mg (44%) of the product as a white solid; LC/MS:532/534 (M+H)+, m.p.: 162-165° C.

後処理

  1. concentrationconcentrated in vacuo
  2. customThe phases are separated
  3. washthe aqueous layer is washed three times with ethyl acetate
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography (SiO2, hexanes/ethyl acetate 1:2)

出典と根拠

ORDレコード
ord-d9b9f75409554070854850951f3f9eaf
出典データセット
uspto-grants-2014_02
特許番号
US08658801B2

反応ノート

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