Potassium Carbonate → HCID 11690028, compound

HRID 2110636Notes

Reaction equation

HRID 2110636 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)[CH:6]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:4]=1.S([CH2:37][N+:38]#[C-:39])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:2][C:3]1[N:4]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH:6]=[C:7]([C:9]2[S:13][C:12]([C:14]3[O:15][CH:39]=[N:38][CH:37]=3)=[CH:11][CH:10]=2)[N:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 11501553HCID 11501553, compound

Product 1

HCID 11690028HCID 11690028, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of 5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-thiophene-2-carbaldehyde [300 mg, 0.81 mmol, Example 8(b)], tosylmethylisocyanide (174 mg, 0.89 mmol), K2CO3 (246 mg 1.78 mmol) and MeOH (30 mL) is heated at reflux for 4 hours. The mixture is allowed to cool to ambient temperature, concentrated by rotary evaporator to remove the solvent. The residue is partitioned between EtOAc and water. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residual solid is subjected to flash column chromatography on silica gel eluting with EtOAc and cyclohexane to afford [2-methoxy-6-(5-oxazol-5-yl-thiophen-2-yl)-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine [240 mg, 73%, Example 11(a)]. LCMS: RT=8.99 minutes, MS: 409 (M+H). IC50=2.3 nM

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. concentrationconcentrated by rotary evaporator
  4. customto remove the solvent
  5. customThe residue is partitioned between EtOAc and water
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bb0958e7f41443168b2e841f05705d6c
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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