Triethylamine → HCID 86724387, compound

HRID 1754386Notes

Reaction equation

HRID 1754386 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]([NH:34][CH3:35])[CH:31]=[N:30]2)=[CH:25][CH:24]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:6]([C:7]([F:8])([F:9])[F:10])=[N:5][N:4]([CH2:17][C:16]([N: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)[CH3:35])=[O:20])[C:3]=1[CH3:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 83877737HCID 83877737, compoundHCID 86724385HCID 86724385, compound

Product 1

HCID 86724387HCID 86724387, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[4-chloro-3-methyl-5-(trifluoromethyl)pyrazol-1-yl]acetic acid (0.070 g, 0.29 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (0.10 mL, 1.16 mmol) and DMF (1 drop). The mixture was stirred for 30 min at room temperature and concentrated in vacuo. The solid obtained was transferred to another flask containing 1-(4-fluorophenyl)-N-methylpyrazol-4-amine (0.056 g, 0.29 mmol) and NEt3 (0.20 mL, 1.4 mmol) in CH2Cl2 (3 mL). The reaction mixture was stirred for 30 min at room temperature, quenched 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/CH2Cl2 gradient elution) to give the title compound (0.045 g, 37%). 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.70 (s, 1H), 7.64 (m, 2H), 7.17 (dd, J=8.4, 8.4 Hz, 2H), 4.80 (s, 2H), 3.28 (s, 3H); MS: (ES) m/z calculated for C17H14ClF4N5O [M+H]+ 416.1, found 416.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe solid obtained
  3. customwas transferred to another flask
  4. stirringThe reaction mixture was stirred for 30 min at room temperature
  5. customquenched with water (50 mL)
  6. extractionextracted with ethyl acetate (50 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by flash chromatography (SiO2, 0-50% EtOAc/CH2Cl2 gradient elution)

Sources & evidence

ORD record
ord-2b7490c23cc64888a9bb543529c46974
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

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