Dimethylformamide → HCID 118513293, compound

HRID 1478809Notes

Reaction equation

HRID 1478809 reaction equation
C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH:12]1([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[N:22]2[C:26]([CH3:27])=[C:25]([C:28]([OH:30])=O)[N:24]=[N:23]2)[CH2:14][CH2:13]1.[NH2:31][C:32]1[C:33](=[O:45])[N:34]([CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[N:35]([CH3:38])[C:36]=1[CH3:37].C(N(CC)CC)C>C(Cl)Cl>[CH:39]1([N:34]2[C:33](=[O:45])[C:32]([NH:31][C:28]([C:25]3[N:24]=[N:23][N:22]([C:16]4[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=4[CH:12]4[CH2:13][CH2:14]4)[C:26]=3[CH3:27])=[O:30])=[C:36]([CH3:37])[N:35]2[CH3:38])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 612730214-amino-2-cyclohexyl-1,5-dimethyl-2,3-dihydro-1H-pyrazol-3-one2×HCID 118513292HCID 118513292, compound

Product 1

HCID 118513293HCID 118513293, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (0.055 ml, 0.632 mmol) in DCM (5 ml) was added DMF (0.065 ml, 0.842 mmol) dropwise and the mixture was stirred for 1 hr. The resulting mixture was treated with 1-(2-cyclopropyl-4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (110 mg, 0.421 mmol) and stirring continued at RT for 30 mins. To the reaction mixture was added 4-amino-2-cyclohexyl-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate A) (97 mg, 0.463 mmol) followed by triethylamine (0.176 ml, 1.263 mmol) and stirring continued at RT for 30 mins. The resulting mixture was diluted with DCM, washed with water and eluted though a phase separating cartridge. The organic eluent was collected and concentrated under reduced pressure to give a brown oil. The was absorbed onto silica and purified by chromatography eluting with 0-10% MeOH in TBME. The product fractions were combined, concentrated and dried under reduced pressure to give a pale brown glassy solid. The solid was dissolved in DCM, washed with water, brine and eluted through a phase separating cartridge. The organic eluent was concentrated under reduced pressure to give the title compound as a glassy solid.

Workup

  1. stirringstirring
  2. waitcontinued at RT for 30 mins
  3. stirringstirring
  4. waitcontinued at RT for 30 mins
  5. washwashed with water
  6. washeluted though a phase
  7. customseparating cartridge
  8. customThe organic eluent was collected
  9. concentrationconcentrated under reduced pressure
  10. customto give a brown oil
  11. customThe was absorbed onto silica
  12. custompurified by chromatography
  13. washeluting with 0-10% MeOH in TBME
  14. concentrationconcentrated
  15. customdried under reduced pressure
  16. customto give a pale brown glassy solid
  17. washwashed with water, brine
  18. washeluted through a phase
  19. customseparating cartridge
  20. concentrationThe organic eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d9eb26deea724c929cedcfa07b03301d
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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