Triethylamine → HCID 86724384, compound

HRID 1754383Notes

Reaction equation

HRID 1754383 reaction equation
[Cl:1][C:2]1[C:3]([CH3:15])=[N:4][N:5](CC(O)=O)[C:6]=1[C:7]([F:10])([F:9])[F:8].[C:16](Cl)(=[O:20])[C:17](Cl)=O.[F:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[C:32]([NH2:34])[CH:31]=[N:30]2)=[CH:25][CH:24]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C.O>[Cl:1][C:2]1[C:6]([C:7]([F:8])([F:9])[F:10])=[N:5][N:4]([CH2:17][C:16]([NH:34][C:32]2[CH:31]=[N:30][N:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[CH:33]=2)=[O:20])[C:3]=1[CH3:15]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 435317151-(4-fluorophenyl)-1H-pyrazol-4-amineHCID 86724385HCID 86724385, compound

Product 1

HCID 86724384HCID 86724384, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-[4-chloro-3-methyl-5-(trifluoromethyl)pyrazol-1-yl]acetic acid (0.150 g, 0.62 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (0.15 mL, 1.75 mmol) and DMF (1 drop). The mixture was stirred for 30 min at room temperature and was then concentrated in vacuo. The solid obtained was transferred to another flask containing 1-(4-fluorophenyl)pyrazol-4-amine (0.080 g, 0.45 mmol) and NEt3 (0.25 mL, 1.8 mmol) in CH2Cl2 (3 mL). The mixture was stirred for 30 min at room temperature, treated with water (50 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (SiO2, 0-50% EtOAc/hexanes gradient elution) to give the title compound as a white solid (0.084 g, 47%). 1H NMR (400 MHz CDCl3) δ 8.40 (s, 1H), 7.71 (s, 1H), 7.69 (m, 2H), 7.19 (dd, J=8.4, 8.4 Hz, 2H), 5.07 (s, 2H), 2.34 (s, 3H); MS: (ES) m/z calculated for C16H12ClF4N5O [M+H]+ 402.0, found 402.0.

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe solid obtained
  3. customwas transferred to another flask
  4. stirringThe mixture was stirred for 30 min at room temperature
  5. extractionextracted with ethyl acetate (50 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography (SiO2, 0-50% EtOAc/hexanes gradient elution)

Sources & evidence

ORD record
ord-08575301ca5845d0afb24fe4fc874763
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

Loading…