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Triethylamine → 4-Amino-5-cyclobutyloxy-6,7-dimethoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline

HRID 1004015
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HRID 1004015 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH3:20])=[C:9]([O:17][CH3:18])[C:10]=2[O:12][CH:13]2[CH2:16][CH2:15][CH2:14]2)[N:5]=[C:4](Cl)[N:3]=1.Cl.[N:23]1([C:29]([N:31]2[CH2:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(N(CC)CC)C>C(O)CCC>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH3:20])=[C:9]([O:17][CH3:18])[C:10]=2[O:12][CH:13]2[CH2:16][CH2:15][CH2:14]2)[N:5]=[C:4]([N:34]2[CH2:35][CH2:36][CH2:37][N:31]([C:29]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[O:30])[CH2:32][CH2:33]2)[N:3]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 184706574-Amino-2-chloro-5-cyclobutyloxy-6,7-dimethoxyquinazolineHCID 227070621-(4-Morpholinecarbonyl)-1,4-diazepane hydrochloride

생성물 1

HCID 184706584-Amino-5-cyclobutyloxy-6,7-dimethoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline수율 386.7%

시약·촉매·용매 1

HCID 2631-Butanol
용매

실험 절차

4-Amino-2-chloro-5-cyclobutyloxy-6,7-dimethoxyquinazoline (184 mg, 0.00059 mol) was added to a solution of 1-(4-morpholinecarbonyl)-1,4-diazepane hydrochloride (163 mg, 0.00065 mol) and triethylamine (184 μl, 0.0013 mol) in n-butanol (6 ml) and the reaction stirred at reflux for 2 hours. On cooling, the reaction was concentrated under reduced pressure and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous layer was further extracted with ethyl acetate (2×20 ml), the combined organic extracts dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified on silica gel eluting with a solvent gradient of methanol:dichloromethane (0:100 to 7:93 v/v) to give the title compound as a white foam (1110 mg, 38%). MS m/z=487 (MH)+. 1H-NMR (CDCl3): δ=1.53 (1H, m), 1.76 (1H, m), 2.04 (2H, m), 2.25 (2H, m), 2.38 (2H, m), 3.20 (4H, t), 3,36 (2H, t), 3.55 (2H, t), 3.66 (4H, t), 3.80 (3H, s), 3.85 (3H, m), 3.94 (6H, m), 4.86 (1H, m), 6.62 (1H, s). Found: C, 58.09; H, 6.96; N, 16.69; C24H34N6O5 0.15CH2Cl2, requires C, 58.09; H, 6.92; N, 16.83%

후처리

  1. temperatureat reflux for 2 hours
  2. temperatureOn cooling
  3. concentrationthe reaction was concentrated under reduced pressure
  4. customthe residue partitioned between ethyl acetate (20 ml) and water (20 ml)
  5. extractionThe aqueous layer was further extracted with ethyl acetate (2×20 ml)
  6. dry with materialthe combined organic extracts dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude product was purified on silica gel eluting with a solvent gradient of methanol:dichloromethane (0:100 to 7:93 v/v)

출처 및 근거

ORD 기록
ord-a47f8a7ec80e46fb8b4dc4c2fc7b8190
출처 데이터셋
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06048864

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