Triethylamine → HCID 57860716, compound

HRID 1513618Notes

Reaction equation

HRID 1513618 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:16])[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:17])[C:4]=1[C:18]([NH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:19].C(N(CC)CC)C.[C:34]([O:37][CH2:38][C:39](Cl)=[O:40])(=[O:36])[CH3:35]>C1COCC1.C(=O)([O-])O.[Na+]>[C:34]([O:37][CH2:38][C:39]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:18]([C:4]2[N:5]([CH3:17])[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][C:8](=[O:16])[C:7]=3[C:3]=2[O:2][CH3:1])=[O:19])[CH2:22][CH2:23]1)=[O:40])(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 66893409HCID 66893409, compound

Product 1

HCID 57860716HCID 57860716, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-methoxy-1-methyl-4-oxo-N-piperidin-4-yl-4,5-dihydro-1H-pyrrolo[3,2-c]quinoline-2-carboxamide (300 mg, 0.87 mmol) and triethylamine (88 mg, 0.87 mmol) in THF (30 mL) was added acetoxyacetyl chloride (119 mg, 0.87 mmol) under ice-cooling, and the mixture was stirred for 2 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The obtained solid was washed with diethyl ether-hexane to give the title compound (221 mg, 56%) as a white solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe obtained solid was washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-578b066fe0d248a49215e1222098d9f6
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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