Water → HCID 178474264, compound

HRID 2205775Notes

Reaction equation

HRID 2205775 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[CH:10]=[C:9]([NH2:11])[NH:8][N:7]=1.CN1CCOCC1.O>C(Cl)Cl>[CH3:5][C:6]1[CH:10]=[C:9]([NH:11][C:1](=[O:3])[CH3:2])[NH:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 178418690HCID 178418690, compound

Product 1

HCID 178474264HCID 178474264, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (41 g, 0.530 mol) was added dropwise to a solution of 3-methyl-1H-pyrazol-5-amine (25.6 g, 0.264 mol) and N-methylmorpholine (58 mL, 0.530 mol) in CH2Cl2 (250 mL) at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 16 h. Water was added to the reaction mixture and the organic layer concentrated in vacuo. The residue was taken up in a mixture of MeOH/THF (100 mL/100 mL), cooled to 10° C. and treated with 1M NaOH solution. The reaction mixture was stirred for 0.25 h, acidified to pH 5 and organic solvents were removed in vacuo. The resulting precipitate was filtered, washed (water, diethyl ether) and dried to provide the title compound as a white solid (29.6 g).

Workup

  1. concentrationthe organic layer concentrated in vacuo
  2. additionThe residue was taken up in a mixture of MeOH/THF (100 mL/100 mL)
  3. temperaturecooled to 10° C.
  4. additiontreated with 1M NaOH solution
  5. stirringThe reaction mixture was stirred for 0.25 h
  6. customwere removed in vacuo
  7. filtrationThe resulting precipitate was filtered
  8. washwashed (water, diethyl ether)
  9. customdried

Sources & evidence

ORD record
ord-7b4347e485ce44c89ae6b18cf2133c3f
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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