Hydrochloric Acid → HCID 135443297, compound

HRID 1355418Notes

Reaction equation

HRID 1355418 reaction equation
[C:1]([C@H:3]([CH3:27])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[N:14]3[CH2:18][CH2:19][N:20](COCC)[C:13]3=[N:12][C:11]=2[N:10]([CH3:25])[C:9]1=[O:26])#[N:2].Cl>C(O)C>[C:1]([C@H:3]([CH3:27])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[N:14]3[CH2:18][CH2:19][NH:20][C:13]3=[N:12][C:11]=2[N:10]([CH3:25])[C:9]1=[O:26])#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69154424HCID 69154424, compound

Product 1

HCID 135443297HCID 135443297, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (R)-3-(5-cyanohexyl)-7,8-dihydro-8-ethoxymethyl-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione and concentrated hydrochloric acid (1.0 ml) and ethanol (5 ml) was stirred at 60° C. for 12 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with ethyl acetate-methanol (3:1) to provide (R)-3-(5-cyanohexyl)-7,8-dihydro-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (CT-30255) (61 mg, 50% yield) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate-methanol (3:1)

Sources & evidence

ORD record
ord-4beff7f9581b447faa149e83704c69a1
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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