Propionyl chloride → HCID 178460002, compound

HRID 1843649

Reaction equation

HRID 1843649 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[C:42](Cl)(=[O:45])[CH2:43][CH3:44].[Na]>O1CCCC1>[F:30][C:29]([F:31])([F:32])[C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20]([NH:19][C:15]2[CH:14]=[C:13]([C:9]3[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:42](=[O:45])[CH2:43][CH3:44])[CH:7]=4)=[CH:12][NH:11][N:10]=3)[CH:18]=[CH:17][CH:16]=2)=[O:21])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 178507322HCID 178507322, compound

Product 1

HCID 178460002HCID 178460002, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

35 mg (0.08 mmol) of 1-{3-[4-(2-aminopyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)-phenyl]urea were dissolved in 2 ml of dry tetrahydrofuran and 27 μl (0.16 mmol) of N,N-diisopropylethylamine and 14 μl of propionyl chloride (0.16 mmol) were added consecutively. The mixture was stirred overnight at room temperature, then poured into aqueous sodium hydrogenocarbonate, extracted with dichloromethane, dried over sodium sulphate ed evaporated. Without any further purification the crude was redissolved with 10 mL of methanol and 5 mL of triethylamine were added. After 7 hours at room temperature the solvent was removed in vacuo, the residue partitioned between dichloromethane and water, dried over sodium sulphate and evaporated. After trituration with diethylether, 30 mg (77%) of the title compound were collected by filtration.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over sodium sulphate
  3. customed evaporated
  4. customWithout any further purification the crude
  5. dissolutionwas redissolved with 10 mL of methanol and 5 mL of triethylamine
  6. additionwere added
  7. customAfter 7 hours at room temperature the solvent was removed in vacuo
  8. customthe residue partitioned between dichloromethane and water
  9. dry with materialdried over sodium sulphate
  10. customevaporated
  11. filtrationAfter trituration with diethylether, 30 mg (77%) of the title compound were collected by filtration

Sources & evidence

ORD record
ord-9832a6d2c6b44982a3c5cc9c49efbec7
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Linked notes

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