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Morpholine → N-(4-(5-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)pyridin-2-yl)morpholine-4-carboxamide

HRID 870453
Notes
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Reaction equation

HRID 870453 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17]([C:19]3[C:20](=[O:32])[N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:22]([CH3:25])[C:23]=3[CH3:24])=[O:18])=[C:11]([Cl:33])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.Cl[C:42](OC1C=CC=CC=1)=[O:43].[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1>C1COCC1>[Cl:33][C:11]1[C:12]([NH:16][C:17]([C:19]2[C:20](=[O:32])[N:21]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:22]([CH3:25])[C:23]=2[CH3:24])=[O:18])=[CH:13][C:14]([F:15])=[C:9]([CH:10]=1)[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:42]([N:51]2[CH2:56][CH2:55][O:54][CH2:53][CH2:52]2)=[O:43])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 73053629N-(4-((2-aminopyridin-4-yl)oxy)-2-chloro-5-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 73053685N-(4-(5-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)pyridin-2-yl)morpholine-4-carboxamide
Yield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-(4-((2-aminopyridin-4-yl)oxy)-2-chloro-5-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (234 mg, 0.5 mmol) and Et3N (0.1 mg, 1 mmol) in THF (5 mL) was added phenyl chloroformate (0.16 mg, 1 mmol). The mixture was stirred at rt for 2 hours, then morpholine (0.44 mL, 5 mmol) was added. The reaction mixture was stirred rt for 24 hours, then partitioned between aq NH4Cl (30 mL) and DCM (30 mL). The organic phase was separated and the aqueous phase extracted with DCM (30 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1) to give the title compound as a white solid (145 mg, 49.9%).

Workup

  1. stirringThe reaction mixture was stirred rt for 24 hours
  2. custompartitioned between aq NH4Cl (30 mL) and DCM (30 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase extracted with DCM (30 mL×3)
  5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1)

Sources & evidence

ORD record
ord-645bca6add15430a9882b225259be6c1
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969388B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes