Dimethylformamide → HCID 118513301, compound

HRID 1478795Notes

Reaction equation

HRID 1478795 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[N:10]=[N:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[NH2:28][C:29]1[C:30](=[O:43])[N:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[F:42])[N:32]([CH3:35])[C:33]=1[CH3:34].C(N(CC)CC)C.CCCC(C)C>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:28][C:29]3[C:30](=[O:43])[N:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[F:42])[N:32]([CH3:35])[C:33]=3[CH3:34])=[O:16])[N:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 6228DimethylformamideHCID 78922-MethylpentaneHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 49799411-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acidHCID 431636614-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one2×

Product 1

HCID 118513301HCID 118513301, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (100 mg, 0.421 mmol), oxalyl chloride (0.041 ml, 0.463 mmol) and DMF (0.065 ml, 0.842 mmol) in dry DCM (5 ml) was added a solution of 4-amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate B) (102 mg, 0.463 mmol) in dry DCM (1 ml), followed by triethylamine (0.176 ml, 1.262 mmol) and the mixture was stirred at RT for 1 hr. The resulting mixture was diluted with DCM and washed with 0.1 M HCl(aq) and sat. NaHCO3(aq). The organic extracts were passed through a phase separating cartridge and concentrated under reduced pressure. The resulting solid was absorbed onto silica and purified by chromatography eluting with 0-10% MeOH in TBME. The product fractions were combined and concentrated under reduced pressure to give a glassy solid, which was suspended in 1:1 iso-hexane:Et2O, heated at 50° C. for 2 h, stoppered and allowed to cool for 16 hrs. The solid was collected by filtration and dried on the vacuum line to give the title compound as a pale yellow solid.

Workup

  1. washwashed with 0.1 M HCl(aq) and sat. NaHCO3(aq)
  2. customseparating cartridge
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting solid was absorbed onto silica
  5. custompurified by chromatography
  6. washeluting with 0-10% MeOH in TBME
  7. concentrationconcentrated under reduced pressure
  8. customto give a glassy solid, which
  9. temperatureto cool for 16 hrs
  10. filtrationThe solid was collected by filtration
  11. customdried on the vacuum line

Sources & evidence

ORD record
ord-aab6f712fa954f6a88eb03c791c4e456
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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