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Cesium carbonate → 3-{[3-chloro-5-(morpholin-4-ylcarbonyl)pyridin-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

HRID 1175976
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HRID 1175976 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@H:24]2[CH2:28][CH2:27][O:26][CH2:25]2)[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12].[Cl:29][C:30]1[CH:31]=[C:32]([C:37]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:38])[CH:33]=[N:34][C:35]=1Cl>C(#N)C>[Cl:29][C:30]1[C:35]([O:7][C:8]2[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@H:24]3[CH2:28][CH2:27][O:26][CH2:25]3)[CH:22]=2)[C:11]([NH:13][C:14]2[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=2)=[O:12])=[N:34][CH:33]=[C:32]([C:37]([N:39]2[CH2:40][CH2:41][O:42][CH2:43][CH2:44]2)=[O:38])[CH:31]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 180701874-(5,6-Dichloropyridine-3-carbonyl)morpholineHCID 591271713-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

생성물 1

HCID 536295683-{[3-chloro-5-(morpholin-4-ylcarbonyl)pyridin-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide수율 76.9%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
120 °C

실험 절차

Cesium carbonate (489 mg, 1.5 mmol) was added to a solution of 3-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (152 mg, 0.5 mmol) and 4-[(5,6-dichloropyridin-3-yl)carbonyl]morpholine (143 mg, 0.55 mmol) in acetonitrile (5 mL) and the mixture heated at 120° C. in a microwave reactor for 2 hours. The acetonitrile was evaporated in vacuo and the residue partitioned between water (25 mL) and ethyl acetate (50 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with ethyl acetate, to give the desired compound (203 mg). 1H NMR δ (CDCl3): 2.05-2.2 (m, 2H), 3.4-3.7 (m, 8H), 3.7 (s, 3H), 3.85 (m, 2H), 3.95 (d, 2H), 4.9 (m, 1H), 6.7 (d, 1H), 6.8 (d, 1H), 7.15 (d, 1H), 7.25 (d, 2H), 7.85 (d, 1H), 8.0 (d, 1H), 8.95 (s, 1H); m/z 512 (M+H)+.

후처리

  1. customThe acetonitrile was evaporated in vacuo
  2. customthe residue partitioned between water (25 mL) and ethyl acetate (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue which
  6. customwas chromatographed on silica
  7. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-c4c44267fa044021b71b981b652c4b9e
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842694B2

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