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Butyric Acid → 5-(4-Butyrylpiperazin-1-yl)carbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrrole

HRID 27083
Notes
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Reaction equation

HRID 27083 reaction equation
[C:1](O)(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl:7][C:8]1[N:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([N:18]3[CH:22]([O:23][C:24]([N:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[O:25])[C:21]4[S:32][CH2:33][CH2:34][S:35][C:20]=4[C:19]3=[O:36])=[N:15]2)=[CH:10][CH:9]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]([N:29]1[CH2:28][CH2:27][N:26]([C:24]([O:23][CH:22]2[N:18]([C:14]3[CH:13]=[CH:12][C:11]4[C:16](=[N:17][C:8]([Cl:7])=[CH:9][CH:10]=4)[N:15]=3)[C:19](=[O:36])[C:20]3[S:35][CH2:34][CH2:33][S:32][C:21]2=3)=[O:25])[CH2:31][CH2:30]1)(=[O:5])[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 10868DicyclohexylcarbodiimideHCID 3085171RP 35489

Product 1

HCID 137286275-(4-Butyrylpiperazin-1-yl)carbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrroleYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Conditions

Temperature
20 °C

Procedure

Butyric acid (0.71 g.) is added to a suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-(piperazin-1-yl)carbonyloxy-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrrole (2.50 g.) and N,N'-dicyclohexyl-carbodiimide (1.67 g.) in anhydrous methylene chloride (50 cc.) and the mixture is stirred for 1 hour at 20° C. After filtering off the dicyclohexylurea formed, washing with methylene chloride (15 cc.) and evaporating the solvent, the residue obtained (3.8 g.) is washed with boiling ethanol (35 cc.) and then recrystallised from a mixture of acetonitrile (110 cc.) and ethanol (11 cc.). 5-(4-Butyrylpiperazin-1-yl)carbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrrole (1.95 g.), which melts at 248° C., is thus obtained.

Workup

  1. filtrationAfter filtering off the dicyclohexylurea
  2. customformed
  3. washwashing with methylene chloride (15 cc.)
  4. customevaporating the solvent
  5. customthe residue obtained (3.8 g.)
  6. washis washed with boiling ethanol (35 cc.)
  7. customrecrystallised from a mixture of acetonitrile (110 cc.) and ethanol (11 cc.)

Sources & evidence

ORD record
ord-156be8bfd6dc4e69a16089b33f19744f
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04220646

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes