Dimethylformamide → HCID 57657251, compound

HRID 244825Notes

Reaction equation

HRID 244825 reaction equation
CN(C=O)C.[NH2:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:25][O:26][CH2:27][CH3:28])[N:19]([CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])[C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([CH2:29][CH2:30][C:31](O)=[O:32])=[CH:10][C:9]=2[N:8]=1.ON1C2C=CC=CC=2N=N1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>O>[NH2:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:25][O:26][CH2:27][CH3:28])[N:19]([CH2:20][C:21]([CH3:23])([OH:24])[CH3:22])[C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([CH2:29][CH2:30][C:31]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[O:32])=[CH:10][C:9]=2[N:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 57657227HCID 57657227, compound

Product 1

HCID 57657251HCID 57657251, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 20-ml glass vial was charged with anhydrous DMF (1 mL), 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoic acid (165 mg, 0.43 mmol), N-(3-dimethylaminopropyl)-N″-ethylcarbodiimide hydrochloride (100 mg, 0.52 mmol, 1.3 eq), 1-hydroxybenzotriazole (70.3 mg, 0.52 mmol, 1.3 eq), and morpholine (110 mg, 1.29 mmol, 3.0 eq). The reaction was maintained at ambient temperature overnight. The reaction mixture was poured into water (10 mL), and the resulting mixture was extracted with dichloromethane (3×10 mL). The chloroform fractions were combined and concentrated, and the residue was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-30% CMA in chloroform) followed by recrystallization from acetonitrile to provide 1-[4-amino-2-(ethoxymethyl)-7-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as a white solid, mp 118-119° C.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane (3×10 mL)
  2. concentrationconcentrated
  3. customthe residue was purified by chromatography
  4. washa HORIZON HPFC system (silica cartridge, eluting with 0-30% CMA in chloroform)
  5. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-cd823ce1a8e94d6fb040373876c1b5c3
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

Loading…