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4-Methylmorpholine → HCID 22710920, compound

HRID 352933
Notes
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Reaction equation

HRID 352933 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[N:9][C:10]([C:13]([OH:15])=O)=[CH:11][N:12]=2)=[CH:3][CH:2]=1.Cl.[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28])=[CH:21]2.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([S:27]([N:30]1[CH2:35][CH2:34][N:33]([C:13]([C:10]3[N:9]=[N:8][C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[N:12][CH:11]=3)=[O:15])[CH2:32][CH2:31]1)(=[O:29])=[O:28])=[CH:21]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22710479HCID 22710479, compoundHCID 227105701-[(5-Chloroindol-2-yl)sulfonyl]piperazine hydrochloride

Product 1

HCID 22710920
HCID 22710920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (10 ml) were suspended 3-(pyridin-4-yl)-1,2,4-triazine-6-carboxylic acid and 1-[(5-chloroindol-2-yl)sulfonyl]piperazine hydrochloride (292 mg) at room temperature. To the reaction mixture were successively added 1-hydroxybenzotriazole (117 mg), N-methylmorpholine (191 μl) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (250 mg), followed by stirring overnight. After completion of the reaction, the solvent was distilled off under reduced pressure. Water and ethyl acetate were added to the residue to separate into layers. The organic layer was dried over magnesium sulfate and the filtrate was concentrated. Ethanol was added to the residue. Yellow crystals thus precipitated were collected by filtration and dried, whereby the free form (282 mg) of the title compound was obtained. The free form was suspended in ethanol and the resulting suspension was made acidic by the addition of 1N hydrochloric acid (in ethanol) and a small amount of water. After concentration of the resulting solution, ethanol and ethyl acetate were added and the resulting mixture was concentrated again. Crystals thus precipitated were collected by filtration and dried, whereby the title compound was obtained.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater and ethyl acetate were added to the residue
  5. customto separate into layers
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationthe filtrate was concentrated
  8. additionEthanol was added to the residue
  9. customYellow crystals thus precipitated
  10. filtrationwere collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-5b75c3835c2e411daf9d2d3e12269bc8
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes