Water → 3-(4-tert-butyl-phenyl)-7-fluoro-2H-pyrrolo[1,2-a]pyrazin-1-one

HRID 2272966Notes

Reaction equation

HRID 2272966 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)=O)[CH:7]=[C:8]([F:10])[CH:9]=1)=O.C([O-])(=O)C.[NH4+:28].O>C(O)(=O)C>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]2[NH:28][C:3](=[O:2])[C:5]3[N:6]([CH:7]=[C:8]([F:10])[CH:9]=3)[CH:11]=2)=[CH:15][CH:16]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 898261481-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 717655383-(4-tert-butyl-phenyl)-7-fluoro-2H-pyrrolo[1,2-a]pyrazin-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 52.4 mg (0.165 mmol) 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester and 382 mg (4.95 mmol) ammonium acetate in 0.5 ml acetic acid is stirred for 18 hours at 110° C. The reaction mixture is allowed to cool to room temperature and excess water is added. The resulting precipitate is filtered off, washed with water and dried. It is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 3-(4-tert-butyl-phenyl)-7-fluoro-2H-pyrrolo[1,2-a]pyrazin-1-one as light brown crystals; HPLC/MS 2.88 min (B), [M+H] 285; 1H NMR (400 MHz, DMSO-d6) δ [ppm] 10.97 (s, 1H), 7.61 (s, 1H), 7.58 (d, J=8.5, 2H), 7.48 (m, 3H), 6.75 (d, J=1.6, 1H), 1.31 (s, 9H).

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with water
  3. customdried
  4. customIt is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-c13c2ab20460492fa9c374a2439b6be1
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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