Potassium Carbonate → HCID 178434860, compound

HRID 2266846Notes

Reaction equation

HRID 2266846 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([C:15]#[N:16])[O:12][C:13]=2[CH3:14])=[CH:3][CH:2]=1.[N-:23]=[N+:24]=[N-:25].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[NH:25][N:24]=[N:23][N:16]=3)[O:12][C:13]=2[CH3:14])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 184446574-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonitrile

Product 1

HCID 178434860HCID 178434860, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonitrile (148) (100 mg, 0.35 mmoles), sodium azide (27 mg, 0.415 mmoles) and potassium carbonate (62 mg, 0.45 mmoles) in dimethylformamide (5 ml) was heated at 90° C. for 96 hours then at 120° C. for 24 hours. The mixture was evaporated and the residue purified by HPLC to afford compound 149 as a white solid (64 mg). LC/MS System D; Rt=9.53 mins, m/2 (ES+)=333 (M+H for C19H16N4O2).

Workup

  1. customThe mixture was evaporated
  2. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-ef30214350e1492f8d2ff536ad5bab6d
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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