Oxalic Acid → HCID 71522658, compound

HRID 2178527Notes

Reaction equation

HRID 2178527 reaction equation
CO[CH2:3][N:4]([CH2:20][Si](C)(C)C)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19].[CH:25]([C:27]1[S:28][CH:29]=[C:30]([CH3:32])[N:31]=1)=[CH2:26].[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35]>ClCCl.C(O)(C(F)(F)F)=O.CC(C)=O>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[CH3:32][C:30]1[N:31]=[C:27]([CH:25]2[CH2:26][CH2:20][N:4]([CH2:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3=[O:19])[CH2:3]2)[S:28][CH:29]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 201470722-Ethenyl-4-methyl-1,3-thiazoleHCID 89500552HCID 89500552, compound

Product 1

HCID 71522658HCID 71522658, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

At 0° C., 1-[2-(2-{(methoxymethyl)[(trimethylsilyl)methyl]amino}ethyl)phenyl]piperidin-2-one a5-2 (696 mg, 2 mmol, 2 eq) is slowly added to 2-ethenyl-4-methyl-1,3-thiazole a5-3 (125 mg, 1 mmol, 1 eq) diluted in dichloromethane/TFA (90 μl/10 μl). The mixture is stirred at room temperature overnight. Solvent is removed under reduced pressure and the residue is purified by basic reverse phase chromatography on silicagel (gradient: acetonitrile/H2O/NH4OH from 30/70/0.1 to 60/40/0.1 in 10 minutes). The product is dissolved in a minimum of acetone and oxalic acid (1 eq) is added to form the salt that is filtered, washed with diethyl ether and dried under vacuum to afford 215 mg of 1-(2-{2-[3-(4-methyl-1,3-thiazol-2-yl)pyrrolidin-1-yl]ethyl}phenyl)piperidin-2-one oxalate 87.

Workup

  1. customSolvent is removed under reduced pressure
  2. customthe residue is purified by basic reverse phase chromatography on silicagel (gradient: acetonitrile/H2O/NH4OH from 30/70/0.1 to 60/40/0.1 in 10 minutes)
  3. additionis added
  4. customto form the salt that
  5. filtrationis filtered
  6. washwashed with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9f37c65979da4be8aa82b3e5cfd82839
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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