Ammonia → HCID 57550525, compound

HRID 1097569Notes

Reaction equation

HRID 1097569 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([NH:20][CH2:21][CH2:22][O:23][CH3:24])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:25]>CO>[NH2:25][C:2]1[C:11]2[N:12]=[C:13]([NH:20][CH2:21][CH2:22][O:23][CH3:24])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86626287HCID 86626287, compound

Product 1

HCID 57550525HCID 57550525, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

1-{4-Chloro-2-[(2-methoxyethyl)amino]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (2.1 g, 6.2 mmol) and ammonia (25 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated overnight in an oven at 150° C. and then allowed to cool to ambient temperature. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluting with 2% methanol in dichloromethane with 1% ammonium hydroxide added.) The isolated product was dried under high vacuum overnight to provide 1.08 g of 1-{4-amino-2-[(2-methoxyethyl)amino]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as a white solid, mp 176-178° C.

Workup

  1. customwhich was sealed
  2. temperatureto cool to ambient temperature
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (eluting with 2% methanol in dichloromethane with 1% ammonium hydroxide added.) The isolated product
  5. customwas dried under high vacuum overnight

Sources & evidence

ORD record
ord-9116e3e04e2e4247a692872a986c6d74
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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