Potassium Carbonate → HCID 59320871, compound

HRID 341198Notes

Reaction equation

HRID 341198 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S([CH2:43][N+:44]#[C-:45])(=O)=O)=CC=1>CO>[O:2]1[C:1]([C:3]2[CH:8]=[CH:7][N:6]3[C:9]([C:12]4[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=4)=[CH:10][N:11]=[C:5]3[CH:4]=2)=[CH:45][N:44]=[CH:43]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 57497682HCID 57497682, compound

Product 1

HCID 59320871HCID 59320871, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[3-(7-Formyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (15 mg, 0.04 mmol), potassium carbonate (11 mg, 0.08 mmol) and TosMic (9.7 mg, 0.05 mmol) were heated in MeOH (2 ml) at 80° C. for 3 h. The reaction mixture was purified using a C18 SPE cartridge, washing with water and eluting the desired compound with MeOH. Removal of the solvent in vacuo afforded the title compound (6 mg). MS: [M+H]+=402

Workup

  1. customThe reaction mixture was purified
  2. washwashing with water
  3. washeluting the desired compound with MeOH
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-f1e75af41cf84fbf8c31196a17feac58
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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