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

HRID 897090Notes

Reaction equation

HRID 897090 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 4) in methanol (150 ml) was treated with aqueous hydrochloric acid (2M, 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 solution (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 magnesium sulphate) and evaporated to give the title compound as a 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 solution (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 magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-836b19bcca8f40f485e5edaa55a12d2b
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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