Morpholine → HCID 14369768, compound

HRID 1381920Notes

Reaction equation

[N:1]1([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[C:9]2[C:4](=NC=[CH:7][CH:8]=2)[N:3]=[CH:2]1.[K].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[CH2:27]([N:29](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:17])=[CH:18][CH:19]=2)[C:9]2[CH:8]=[CH:7][N:29]=[CH:27][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: -5 °C

Procedure

A stirred suspension of 4-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)benzoic acid, potassium salt (0.50 g, 0.00172 mol) in dry dimethylformamide (5 ml) was treated with morpholine (0.19 g, 0.00214 mol) and triethylamine (0.36 g, 0.00356 mol). The reaction mixture was then cooled to -5° C. and treated with diphenylphosphoryl azide (0.54 g, 0.00196 mol). The resulting mixture was allowed to warm up to room temperature and stirred for an additional 15 hours. The solvent and excess reagents were evaporated off under reduced pressure to yield a crude product which was purified by column chromatography (silica gel, 10% ethanol in chloroform) and recrystallized from ethyl acetate to yield [4-(1H-imidazo[4,5-c]pyridin-1-ylmethyl)phenyl](4-morpholinyl)methanone as a colorless crystalline solid, having a melting point of 119°-121° C. and the following physical characteristics:

Workup

temperatureto warm up to room temperature
customThe solvent and excess reagents were evaporated off under reduced pressure
customto yield a crude product which
customwas purified by column chromatography (silica gel, 10% ethanol in chloroform)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-ec63c333f542479b88652df9fbfd9a11
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04804658

Reaction notes

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