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

HRID 2272973Notes

Reaction equation

HRID 2272973 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:12][C:13]([C:15]2[CH:16]=[N:17][N:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:19]=2)=O)[CH:8]=[C:9]([CH3:11])[CH:10]=1)=O)C.C([O-])(=O)C.[NH4+:28].O>C(O)(=O)C>[C:20]([N:18]1[CH:19]=[C:15]([C:13]2[NH:28][C:4](=[O:3])[C:6]3[N:7]([CH:8]=[C:9]([CH3:11])[CH:10]=3)[CH:12]=2)[CH:16]=[N:17]1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 898261431-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 717650853-(1-tert-butyl-1H-pyrazol-4-yl)-7-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 375 mg (1.18 mmol) 1-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester and 4.89 g (63.5 mmol) ammonium acetate in 4.15 ml acetic acid is stirred for 28 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-(1-tert-butyl-1H-pyrazol-4-yl)-7-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one as light yellow solid; HPLC/MS 2.27 min (B), [M+H] 271;

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-8b6fa2d5fe1545daa265515fb7189834
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

Loading…