Triethylamine → HCID 117974955, compound

HRID 2206853Notes

Reaction equation

HRID 2206853 reaction equation
[CH:1]([CH:4]1[C:8]2[C:9]([NH2:13])=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([CH3:15])([CH3:14])[O:5]1)([CH3:3])[CH3:2].C(N(CC)CC)C.[F:23][C:24]1[N:28]([CH3:29])[N:27]=[C:26]([CH:30]([F:32])[F:31])[C:25]=1[C:33](Cl)=[O:34]>C(Cl)Cl>[F:32][CH:30]([F:31])[C:26]1[C:25]([C:33]([NH:13][C:9]2[C:8]3[CH:4]([CH:1]([CH3:3])[CH3:2])[O:5][C:6]([CH3:15])([CH3:14])[C:7]=3[CH:12]=[CH:11][CH:10]=2)=[O:34])=[C:24]([F:23])[N:28]([CH3:29])[N:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chlorideHCID 90023275HCID 90023275, compound

Product 1

HCID 117974955HCID 117974955, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 25 ml round bottom flask, a solution of 3-isopropyl-1,1-dimethyl-1,3-dihydro-2-benzofuran-4-amine (62 mg, 0.301 mmol, 1 eq) in 5 ml of DCM is cooled to 0° C. and triethylamine (0.05 ml, 0.361 mmol, 1.2 eq) is added. A solution of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride (70 mg, 0.331 mmol, 1.1 eq) in 1 ml of DCM is added dropwise. Stirring is allowed for 4 h at r.t. The reaction is quenched with 1N aq. HCl, and diluted with EtOAc. The aqueous layer was separated and extracted with EtOAc. The organics were combined, washed with NaOH 1N, dried over MgSO4 and concentrated. The crude material was purified by chromatography on silica gel to give pure material (78%)

Workup

  1. customThe reaction is quenched with 1N aq. HCl
  2. additiondiluted with EtOAc
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. washwashed with NaOH 1N
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-041194807c2947a3a04eda39d38f3d03
Source dataset
uspto-grants-2016_06
Patent number
US09375006B2

Reaction notes

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