Hydrochloric Acid → HCID 59441720、化合物

HRID 1014432

反応式

HRID 1014432 の反応式
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=2[C:24]([NH2:26])=[O:25])[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[CH3:32][N:33]([CH2:35][C:36]([N:38]1[C:46]2[C:41](=[CH:42][C:43]([O:48][CH3:49])=[C:44]([NH2:47])[CH:45]=2)[CH2:40][CH2:39]1)=[O:37])[CH3:34].Cl.O1CCOCC1>FC(F)(F)CO.[NH4+].[OH-].C1COCC1>[CH3:32][N:33]([CH3:34])[CH2:35][C:36]([N:38]1[C:46]2[C:41](=[CH:42][C:43]([O:48][CH3:49])=[C:44]([NH:47][C:2]3[N:3]=[C:4]([NH:21][C:22]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=4[C:24]([NH2:26])=[O:25])[C:5]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=5)(=[O:13])=[O:12])[C:6]=4[N:7]=3)[CH:45]=2)[CH2:40][CH2:39]1)=[O:37]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 534147641-(6-Amino-5-methoxy-2,3-dihydro-1H-indol-1-yl)-2-(dimethylamino)ethan-1-oneHCID 86644188HCID 86644188、化合物

生成物 1

HCID 59441720HCID 59441720、化合物収率 51%

試薬・触媒・溶媒 3

HCID 64092,2,2-Trifluoroethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 14923Ammonium Hydroxide溶媒

実験手順

A mixture of 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide (11 g, 24 mmol), 1-[(dimethylamino)acetyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (5 g, 20 mmol), a 4M HCl solution in dioxane (25 mL, 100 mmol) and 2,2,2-trifluoroethanol (250 mL) was heated at 80° C. for 16 h. The resulting mixture was allowed to cool to rt and diluted with a 27% aqueous NH4OH solution (250 mL) and THF (250 mL). The reaction mixture was stirred at rt overnight. The resulting slurry was filtered and the solids were triturated using H2O (300 mL), Et2O (300 mL) and finally EtOAc (300 mL). The solids were dissolved in THF, concentrated onto Celite and purified by silica gel chromatography using 0-10% MeOH (containing 0.2% NH3)/CH2Cl2. The solids obtained following chromatography were triturated using a mixture of MeOH and CH2Cl2to afford 2-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide as a beige solid (6.8 g, 51%).

後処理

  1. filtrationThe resulting slurry was filtered
  2. customthe solids were triturated
  3. dissolutionThe solids were dissolved in THF
  4. concentrationconcentrated onto Celite
  5. custompurified by silica gel chromatography
  6. customThe solids obtained
  7. customwere triturated
  8. additiona mixture of MeOH and CH2Cl2to

出典と根拠

ORDレコード
ord-6f4dab0240e74e02b912d78f19234777
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

関連ノート

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