Dimethylamine → HCID 178482550, compound

HRID 493710Notes

Reaction equation

HRID 493710 reaction equation
[CH:1]([C:3]1[S:7]/[C:6](=[N:8]\[CH3:9])/[N:5]([CH3:10])[C:4]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=O.[CH3:25][NH:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.ClCCCl.C(O)(=O)C>[CH3:25][N:26]([CH2:1][C:3]1[S:7]/[C:6](=[N:8]\[CH3:9])/[N:5]([CH3:10])[C:4]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[CH3:27]

Participants

7

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 178482551HCID 178482551, compound

Product 1

HCID 178482550HCID 178482550, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(((2Z)-5-formyl-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-4-yl)methyl)piperazine-1-carboxylate (1.0 g) obtained in Example 35a) and a 1 M solution of dimethylamine in THF (2.6 mL) were dissolved in a mixed solution of 1,2-dichloroethane (50 mL) and acetic acid (0.18 mL). Triacetoxy sodium borohydride (0.84 g) was added thereto at 0° C., and the mixture was mixed at room temperature overnight. The reaction solution was basified with an aqueous potassium carbonate solution, then extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off to give the title compound (1.1 g) as pale brown crystals.

Workup

  1. additionat 0° C., and the mixture was mixed at room temperature overnight
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-e78247c8a9504dfa99338f1e3cb3f9ca
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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