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Cesium carbonate → 6-(N,N-Diethylcarbamoylmethoxy)-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline

HRID 1357710
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HRID 1357710 반응식
Cl[CH2:2][C:3]([N:5]([CH2:8][CH3:9])[CH2:6][CH3:7])=[O:4].[OH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]2[NH:23][C:24]1[CH:29]=[C:28]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[CH:34]=2)=[O:32])[CH:27]=[CH:26][C:25]=1[CH3:45].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[CH2:6]([N:5]([CH2:8][CH3:9])[C:3]([CH2:2][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]2[NH:23][C:24]1[CH:29]=[C:28]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([N:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)[CH:34]=2)=[O:32])[CH:27]=[CH:26][C:25]=1[CH3:45])=[O:4])[CH3:7]
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참가 물질

5

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HCID 10796Cesium carbonateHCID 16844Chloro-N,N-diethylacetamideHCID 227322826-Hydroxy-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline

생성물 1

HCID 227322966-(N,N-Diethylcarbamoylmethoxy)-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline수율 21.6%

시약·촉매·용매 1

HCID 31374
Dimethylacetamide
용매

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온도
100 °C

실험 절차

2-Chloro-N,N-diethylacetamide (0.05 g) was added to a mixture of 6-hydroxy-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline (0.15 g), cesium carbonate (0.3 g) and dimethylacetamide (2 ml) and the reaction mixture was stirred and heated to 100° C. for 18 hours. After cooling to ambient temperature the reaction mixture was partitioned between methylene chloride and water. The organic layer was dried with brine and sodium sulphate, filtered and evaporated. The residual gum was triturated under diethyl ether. There was thus obtained the title compound as a solid (0.04 g, 20%); NMR: 1.05 (t, 3H), 1.4 (t, 3H), 2.13 (s, 3H), 3.35 (m, 4H), 3.51 (m, 4H), 3.7 (m, 4H), 3.95 (s, 3H), 4.91 (s, 2H), 7.11 (m, 1H), 7.18 (s, 1H), 7.24 (s, 1H), 7.29 (m, 1H), 7.6 (m, 1H), 7.77 (m, 2H), 8.26 (m, 2H), 9.3 (broad s, 1H), 10.32 (broad s, 1H); m/s: M+H+ 600.

후처리

  1. temperatureAfter cooling to ambient temperature the reaction mixture
  2. customwas partitioned between methylene chloride and water
  3. dry with materialThe organic layer was dried with brine and sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residual gum was triturated under diethyl ether

출처 및 근거

ORD 기록
ord-66d703534c0a4d7da9a66add5f5b04c6
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06593333B1

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