Morpholine → HCID 178482549, compound

HRID 493711Notes

Reaction equation

HRID 493711 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.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl.C(O)(=O)C>[CH3:10][N:5]1[C:4]([CH2:11][N:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17]2)=[C:3]([CH2:1][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[S:7]/[C:6]/1=[N:8]\[CH3:9]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 178482551HCID 178482551, compound

Product 1

HCID 178482549HCID 178482549, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

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 morpholine (0.36 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 (1.2 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-dd4d3e3f95444b8d8913f6b8b4492493
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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