Dimethyl Sulfate → HCID 23023985, compound

HRID 1373853Notes

Reaction equation

HRID 1373853 reaction equation
[CH3:1]N(C)C(=O)C.[CH:7]1([C:13]2[CH:44]=[CH:43][C:16]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:26]=[C:27]([N:30]([CH2:32][C:33]5[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=5)[CH3:31])[S:28][CH:29]=4)=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CCCCCC>[CH:7]1([C:13]2[CH:44]=[CH:43][C:16]([CH2:17][N:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:26]=[C:27]([N:30]([CH2:32][C:33]5[CH:34]=[CH:35][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:41][CH:42]=5)[CH3:31])[S:28][CH:29]=4)=[CH:21][CH:20]=3)[CH3:1])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 6497Dimethyl Sulfate2×HCID 11430Potassium Carbonate2×HCID 31374DimethylacetamideHCID 23024001HCID 23024001, compound

Product 1

HCID 23023985HCID 23023985, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Under an argon stream, N,N-dimethylacetamide (351 ml, 5.0 v/w) was added to methyl 4-(N-(4-(4-(4-cyclohexylbenzylamino)phenyl)-2-thiazolyl)-N-methylaminomethyl)benzoate (70.3 g, 0.134 mol) obtained in Example 1(5) and potassium carbonate (73.9 g, 0.535 mol) was carefully added with stirring. After stirring the mixture at room temperature for 20 min., dimethyl sulfate (50.6 ml, 0.535 mol) was added. After stirring at 50° C. for 1 hr., potassium carbonate (18.4 g, 0.134 mol) and dimethyl sulfate (12.7 ml, 0.134 mol) were added and the mixture was stirred at 60° C. for 2 hr. After cooling to room temperature, n-hexane (422 ml, 6.0 v/w) was added, and the mixture was stirred for 1 hr. After ice-cooling, distilled water (562 ml, 8.0 v/w) was added. After stirring at room temperature for 1 hr., the resulting crystals were collected by filtration and washed with methanol (352 ml, 5.0 v/w) in a slurry form. Tetrahydrofuran (180 ml) was added to the obtained orange solid and insoluble materials were filtered off. The filtrate was concentrated to give the title compound (42.1 g, yield 58.3%) as a pale-yellow solid.

Workup

  1. additionwas carefully added
  2. stirringAfter stirring the mixture at room temperature for 20 min.
  3. stirringAfter stirring at 50° C. for 1 hr
  4. stirringthe mixture was stirred at 60° C. for 2 hr
  5. stirringthe mixture was stirred for 1 hr
  6. temperatureAfter ice-cooling
  7. distillationdistilled water (562 ml, 8.0 v/w)
  8. additionwas added
  9. stirringAfter stirring at room temperature for 1 hr
  10. filtration, the resulting crystals were collected by filtration
  11. washwashed with methanol (352 ml, 5.0 v/w) in a slurry form
  12. additionTetrahydrofuran (180 ml) was added to the obtained orange solid and insoluble materials
  13. filtrationwere filtered off
  14. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d60b2ba80dd44514b3ecbc75bd4229d5
Source dataset
uspto-grants-2007_01
Patent number
US07163952B2

Reaction notes

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