2-Chloroquinazoline → HCID 57662924, 화합물

HRID 406845

반응식

HRID 406845 반응식
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[N:17]([C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])[C:16]2=[O:31]>C(O)CCC>[CH3:29][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:30])[C:23]=1[N:17]1[C:16](=[O:31])[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([NH:12][C:2]3[N:11]=[C:10]([C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)[CH:14]=2)[C:18]1=[O:22]

참가 물질

4

반응물 2

HCID 740542-ChloroquinazolineHCID 1240314-Amino-N-(2,6-dimethylphenyl)phthalimide

생성물 1

HCID 57662924HCID 57662924, 화합물수율 42.5%

시약·촉매·용매 1

HCID 2631-Butanol용매2회

실험 절차

A mixture of 2-chloroquinazoline (0.62 g, 2.6 mmol) and 5-amino-2-(2,6-dimethylphenyl)isoindoline-1,3-dione (0.69 g, 2.6 mmol) in n-butanol (10 mL) was heated at 120° C. until all of the butanol had evaporated. Additional butanol (10 mL) was added and the process repeated twice. After the reaction mixture was cooled, water was added (20 mL). A precipitate which formed was collected by suction filtration. N,N-Dimethylacetamide (5 mL) was added to dissolve the solid which was purified by preparative reverse-phase HPLC to give 2-(2,6-dimethylphenyl)-5-[(4-phenylquinazolin-2-yl)amino]-1H-isoindole-1,3(2H)-dione (0.26 g, 21%). 1H NMR (400 MHz, DMSO-d6): δ 10.88 (s, 1H), 8.80 (m, 1H), 8.42 (m, 1H), 7.96 (m, 1H), 7.90 (m, 2H), 7.85 (m, 1H), 7.81 (m, 2H), 7.65 (m, 3H), 7.50 (m, 1H), 7.32 (m, 1H), 7.25 (m, 2H), 2.10 (s, 6H). MS (EI) for C30H22N4O2: 471.0 (MH+).

후처리

  1. customhad evaporated
  2. additionAdditional butanol (10 mL) was added
  3. temperatureAfter the reaction mixture was cooled
  4. additionwater was added (20 mL)
  5. customA precipitate which formed
  6. filtrationwas collected by suction filtration
  7. additionN,N-Dimethylacetamide (5 mL) was added
  8. dissolutionto dissolve the solid which
  9. customwas purified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-314e9a87e0de4aa19734bdec3432787e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754092B2

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