Piperidine → HCID 57597137, compound

HRID 1926006Notes

Reaction equation

HRID 1926006 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][CH2:23][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][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8082Piperidine2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 57597313HCID 57597313, compound

Product 1

HCID 57597137HCID 57597137, 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), piperidine (0.078 mL), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (173 mg) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 hrs. Piperidine (0.078 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 to give the title compound (78 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

Sources & evidence

ORD record
ord-3e38a296201f439c81b8005c8bda5659
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

Loading…