Thiomorpholine → HCID 57597348, compound

HRID 1926007Notes

Reaction equation

HRID 1926007 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][NH:9][C:5]=2[C:4]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)=[N:3][CH:2]=1.[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>[Cl-].[Na+].O.CN(C)C=O>[N:20]1([C:14]([C:13]2[CH:12]=[C:11]([NH:10][C:4]3[C:5]4[NH:9][CH:8]=[CH:7][C:6]=4[N:1]=[CH:2][N:3]=3)[CH:19]=[CH:18][CH:17]=2)=[O:16])[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 67164Thiomorpholine2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 57597313HCID 57597313, compound

Product 1

HCID 57597348HCID 57597348, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoic acid (153 mg), thiomorpholine (0.091 mL), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (173 mg) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 hrs. Thiomorpholine (0.030 mL) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (173 mg) were added and the mixture was stirred for 1 hr. 1-Hydroxybenzotriazole (138 mg) was added, and the mixture was stirred for 3 days. Saturated brine was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→20:80). Diisopropyl ether was added and the precipitate was collected by filtration. The precipitate was dissolved in ethyl acetate containing methanol, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue and the precipitate was collected by filtration to give the title compound (82 mg) as a pale-brown powder.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. stirringthe mixture was stirred for 3 days
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→20:80)
  8. additionDiisopropyl ether was added
  9. filtrationthe precipitate was collected by filtration
  10. dissolutionThe precipitate was dissolved in ethyl acetate
  11. additioncontaining methanol
  12. washwashed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  15. additionwas added to the obtained residue
  16. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-bab1708509d04b648f840d5cc57bc364
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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