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4-Chloroquinazoline → 7-(2-Methoxyethoxy)-4-(2-methyl-3-(quinazolin-4-ylamino)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361290
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HRID 2361290 반응식
[NH2:1][C:2]1[C:3]([CH3:29])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][C:16]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:17][CH:18]=4)[NH:13][C:12]=3[C:11]([C:26]([NH2:28])=[O:27])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl[C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[CH:33][N:32]=1>CC(O)C.C(OCC)(=O)C>[CH3:25][O:24][CH2:23][CH2:22][O:21][C:16]1[CH:15]=[C:14]2[C:19]([C:20]3[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:31]5[C:40]6[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=6)[N:34]=[CH:33][N:32]=5)[C:3]=4[CH3:29])=[CH:9][N:10]=[C:11]([C:26]([NH2:28])=[O:27])[C:12]=3[NH:13]2)=[CH:18][CH:17]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 788644-ChloroquinazolineHCID 679945404-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

생성물 1

HCID 547665687-(2-Methoxyethoxy)-4-(2-methyl-3-(quinazolin-4-ylamino)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide수율 25.5%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate
용매

반응 조건

온도
115 °C

실험 절차

A mixture of 4-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide (51 mg, 0.131 mmol), and 4-chloroquinazoline (47.3 mg, 0.287 mmol) in 2-Propanol (5 mL) was heated at 115° C. under microwave for 30 min. The mixture was diluted with ethyl acetate (80 mL), washed with saturated NaHCO3 solution (20 mL) and brine (20 mL), and dried over anhydrous MgSO4. The solvent was removed under vacuum, and the residue was purified by reverse phase HPLC. The correct fractions were concentrated under vacuum, basified with saturated NaHCO3 solution, and extracted with ethyl acetate (3×30 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (18.0 mg, 0.033 mmol, 25.5% yield) as a yellow solid. LCMS (M+H)+=519.30. 1H NMR (500 MHz, DMSO-d6) δ: 11.65 (s, 1H), 10.17 (s, 1H), 8.61 (s, 1H), 8.55 (d, J=8.0 Hz, 1H), 8.29 (s, 1H), 8.19 (s, 1H), 7.89 (m, 1H), 7.80 (d, J=8.3 Hz, 1H), 7.75 (s, 1H), 7.66 (m, 1H), 7.55-7.49 (m, 2H), 7.38-7.36 (m, 2H), 7.33 (d, J=8.9 Hz, 1H), 6.80 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 4.17 (m, 2H), 3.73 (m, 2H), 3.34 (s, 3H), 1.87 (s, 3H).

후처리

  1. washwashed with saturated NaHCO3 solution (20 mL) and brine (20 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by reverse phase HPLC
  5. concentrationThe correct fractions were concentrated under vacuum
  6. extractionextracted with ethyl acetate (3×30 mL)
  7. extractionThe combined extract
  8. washwas washed with brine (30 mL)
  9. dry with materialdried over anhydrous MgSO4
  10. customRemoval of solvent under vacuum

출처 및 근거

ORD 기록
ord-c5b29c1bb3e84848b7ab2429d451dcaf
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08685969B2

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