Potassium Carbonate → HCID 89767420, compound

HRID 1752514Notes

Reaction equation

HRID 1752514 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:30][C:31]1[S:32][CH:33]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[N:35]=1>C(#N)C.CCOC(C)=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:30][C:31]2[S:32][CH:33]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[N:35]=2)[CH2:19][CH2:18]1)=[O:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 25067319Methyl 2-(chloromethyl)-1,3-thiazole-4-carboxylateHCID 89767058HCID 89767058, compound

Product 1

HCID 89767420HCID 89767420, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Finally, a mixture of compound 7b (637 mg, 1.96 mmoles) and potassium carbonate (813 mg, 5.88 mmoles) in acetonitrile (5 mL) was heated to reflux for 1 hour, then a solution of methyl 2-(chloromethyl)-1,3-thiazole-4-carboxylate (500 mg, 2.6 mmoles) in acetonitrile (5 mL) was added dropwise. The mixture was refluxed overnight then was cooled, diluted with EtOAc and filtered. The resulting solid was washed with water, dried and purified via flash chromatography (silica, from CHCl3 to CHCl3:MeOH 9:1) providing 280 mg (32% yield) of methyl 2-{[4-({[(5-methoxy-1H-indazol-3-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}-1,3-thiazole-4-carboxylate 7.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was refluxed overnight
  4. temperaturethen was cooled
  5. filtrationfiltered
  6. washThe resulting solid was washed with water
  7. customdried
  8. custompurified via flash chromatography (silica, from CHCl3 to CHCl3:MeOH 9:1)

Sources & evidence

ORD record
ord-61e4897006d3432cb602c3dbac010733
Source dataset
uspto-grants-2015_10
Patent number
US09163013B2

Reaction notes

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