Ammonium Acetate → HCID 71765426, compound

HRID 2272951Notes

Reaction equation

HRID 2272951 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:10][C:11](=O)[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1)=O.C([O-])(=O)C.[NH4+:27]>C(O)(=O)C>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([C:11]2[NH:27][C:3](=[O:2])[C:5]3[N:6]([CH:7]=[CH:8][CH:9]=3)[CH:10]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 89826318HCID 89826318, compound

Product 1

HCID 71765426HCID 71765426, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 106 mg (0.34 mmol) 1-[2-oxo-2-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrole-2-carboxylic acid methyl ester and 789 mg (10.2 mmol) ammonium acetate in 2 ml acetic acid is heated to 80° C. under stirring. The mixture is stirred at this temperature for 5 hours and then cooled to room temperature. The mixture is partitioned between THF and saturated sodium chloride solution. The organic phase is washed two times with 25% aqueous ammonia and two times with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 3-(4-trifluoromethyl-phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one as colourless crystals; HPLC/MS 2.11 (A), [M+H] 279;

Workup

  1. stirringThe mixture is stirred at this temperature for 5 hours
  2. customThe mixture is partitioned between THF and saturated sodium chloride solution
  3. washThe organic phase is washed two times with 25% aqueous ammonia and two times with saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-b44f1f31c713456eaf17200e75532b4b
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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