HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → N-(10-methoxymethyl-10H-Pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl) chloro-acetamide

HRID 1059371
Notes
Print preview

Reaction equation

HRID 1059371 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30].O>CN(C)C=O.ClCCl>[CH3:18][O:17][CH2:16][N:8]1[C:7]2[CH:19]=[C:3]([CH2:2][NH:1][C:29](=[O:30])[CH2:28][Cl:27])[CH:4]=[CH:5][C:6]=2[S:11][C:10]2[N:12]=[CH:13][CH:14]=[N:15][C:9]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 186704238-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 1

HCID 23565184N-(10-methoxymethyl-10H-Pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl) chloro-acetamide

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

1.25 g of 8-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and 0.7 ml of triethylamine were dissolved in N,N-dimethylformamide (15 ml). Under ice-cooling, 2 ml of a solution of 0.4 ml of chloroacetyl chloride in dichloromethane was dropped thereinto and the resulting mixture was stirred for 1 hour. After adding water, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate). The crystals thus obtained were washed with n-hexane and thus 1.28 g of the title compound was obtained as a yellow powder.

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  5. concentrationAfter concentrating under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)
  7. customThe crystals thus obtained
  8. washwere washed with n-hexane

Sources & evidence

ORD record
ord-f6608daa2c554987a8f6fd222c3cb18a
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06518423B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes