Thionyl Chloride → HCID 57593710、化合物

HRID 1785331ノート

反応式

HRID 1785331 の反応式
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:4])=[O:3].S(Cl)(Cl)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]2[N:34]=[C:33]([NH:35][CH2:36][CH2:37][C:38]3[NH:39][CH:40]=[N:41][CH:42]=3)[C:32]([Br:43])=[CH:31][N:30]=2)=[CH:24][CH:23]=1>CC(N(C)C)=O>[Br:43][C:32]1[C:33]([NH:35][CH2:36][CH2:37][C:38]2[NH:39][CH:40]=[N:41][CH:42]=2)=[N:34][C:29]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:9](=[O:11])[C:8]3[CH:12]=[CH:13][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=3)=[CH:27][CH:26]=2)=[N:30][CH:31]=1

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 27238714-(Methanesulfonyl)-3-nitrobenzoic acidHCID 57593472N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)ethyl]pyrimidine-2,4-diamine

生成物 1

HCID 57593710HCID 57593710、化合物収率 23.7%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

4-Methanesulfonyl-3-nitro-benzoic acid (72 mg, 0.29 mmole) was dissolved in DMA (3 ml) and thionyl chloride (0.29 mmole) was added at ambient temperature. After the mixture was stirred for 5 minutes N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (100 mg, 0.26 mmole, prepared according to procedure 21) was added and the reaction was allowed to stir overnight. After extraction with bicarbonate solution and ethyl acetate (3×) the combined organic layers were dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by flashmaster chromatography on silica gel to provide 37 mg of N-(4-{5-Bromo-4-[2-(3H-imidazol-4-yl)-ethylamino]-pyrimidin-2-ylamino}-phenyl}-4-methanesulfonyl-3-nitro-benzamide (23% yield). ESI-MS: 602.

後処理

  1. additionwas added
  2. extractionAfter extraction with bicarbonate solution and ethyl acetate (3×) the combined organic layers
  3. dry with materialwere dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flashmaster chromatography on silica gel

出典と根拠

ORDレコード
ord-7374dfe2c0c34fff95de0663074bc577
出典データセット
uspto-grants-2009_03
特許番号
US07504410B2

反応ノート

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