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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 1011804
Notes
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Reaction equation

HRID 1011804 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 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]benzamideYield 76.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-6453132bf3bc43d9a675a662c89fe53b
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977328B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes