Hydrochloric Acid → N-({6-[(2,2-Diphenylethyl)amino]-9H-purin-2-yl}methyl)-N'-[2-(1-piperidinyl)ethyl]urea

HRID 1168310Notes

Reaction equation

HRID 1168310 reaction equation
[C:1]1([CH:7]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([CH2:19][NH:20][C:21]([NH:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:22])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3C2CCCCO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CO>[C:38]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([CH2:19][NH:20][C:21]([NH:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:22])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21360613N-({6-[(2,2-Diphenylethyl)amino]-9-tetrahydro-2H-pyran-2-yl-9H-purin-2-yl}methyl)-N'-[2-(1-piperidinyl)ethyl]urea

Product 1

HCID 178523406N-({6-[(2,2-Diphenylethyl)amino]-9H-purin-2-yl}methyl)-N'-[2-(1-piperidinyl)ethyl]ureaYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-({6-[(2,2-diphenylethyl)amino]-9-tetrahydro-2H-pyran-2-yl-9H-purin-2-yl}methyl)-N′-[2-(1-piperidinyl)ethyl]urea (300 mg, 0.51 mmol) (Preparation 41) in methanol (150 ml) was treated with 2 molar aqueous hydrochloric acid (100 ml). The reaction mixture was stirred at room temperature for 2 hours. The solvent volume was then reduced to 100 ml by evaporation under reduced pressure. Saturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (200 ml) were added. The two phases were separated. The organic layer was washed with saturated aqueous sodium chloride solution (100 ml), dried (anhydrous MgSO4) and evaporated to give the title compound as a white solid (255 mg).

Workup

  1. customThe solvent volume was then reduced to 100 ml by evaporation under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (200 ml) were added
  3. customThe two phases were separated
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution (100 ml)
  5. dry with materialdried (anhydrous MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c894fe453f8046999f36b79b20f90cb1
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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