Ethyl orthoformate → HCID 178461174, compound

HRID 1696261Notes

Reaction equation

HRID 1696261 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9](=[O:18])[N:10]([C@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]3[CH3:17])[C:4]=2[C:3]=1[NH2:19].[CH2:20](OC(OCC)OCC)C>Cl>[CH3:17][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@@H:11]1[N:10]1[C:4]2=[C:3]3[N:19]=[CH:20][NH:1][C:2]3=[N:7][CH:6]=[C:5]2[NH:8][C:9]1=[O:18]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 67278322HCID 67278322, compound

Product 1

HCID 178461174HCID 178461174, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 6,7-diamino-1-[(1S,2R)-2-methylcyclohexyl]-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (40 mg), orthoformic acid triethyl ester (1 mL) and HCl (20 uL) was stirred at ambient temperature for an hour. The mixture was concentrated under reduced pressure. The residue was purified by column chromatography (NH2 silica gel, chloroform:methanol=95:5) to give 8-[(1S,2R)-2-methylcyclohexyl]-6,8-dihydrodiimidazo[4,5-b:4′,5′-d]pyridin-7(3H)-one (21 mg) as a white powder.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography (NH2 silica gel, chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-9d1f08a7de644f43a64e3de646b94b87
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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