Hydrochloric Acid → HCID 59441720, 화합물

HRID 1014432

반응식

HRID 1014432 반응식
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]

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 59441720HCID 59441720, 화합물수율 51%

시약·촉매·용매 3

HCID 64092,2,2-Trifluoroethanol용매HCID 8028Tetrahydrofuran용매HCID 14923Ammonium Hydroxide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6f4dab0240e74e02b912d78f19234777
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

연결된 노트

불러오는 중…