Dimethylformamide → HCID 46912604, compound

HRID 925579Notes

Reaction equation

HRID 925579 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)[CH:18]=3)=[N:8][C:7]=2[NH:6][C:5]1=[O:30])[CH2:2][CH3:3].[F:31][CH:32]([F:37])C(OCl)=O.[Na].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>O>[F:31][CH:32]([F:37])[O:30][C:5]1[N:4]([CH2:1][CH2:2][CH3:3])[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[CH:21]=4)[CH:18]=3)=[N:8][C:7]=2[N:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 10158974HCID 10158974, compoundHCID 86664817HCID 86664817, compound

Product 1

HCID 46912604HCID 46912604, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-Propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-3,7-dihydro-purine-2,6-dione (100 mg, 0.24 mmol), Sodium chloro difluoroacetate (47 mg, 0.31 mmol), Cs2CO3 (117 mg, 0.36 mmol) and DMF (2 ml) were stirred at 60° C. for 18 hours. Reaction mixture was cooled and diluted with water (10 ml), solid materials were filtered off and it was purified by preparative HPLC to obtain 2-Difluoromethoxy-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one as off white solid (1 mg, 10%) and

Workup

  1. customReaction mixture
  2. temperaturewas cooled
  3. filtrationwere filtered off
  4. customit was purified by preparative HPLC

Sources & evidence

ORD record
ord-67a82472253d4e249c97573ab760b36d
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

Loading…