Potassium Bicarbonate → HCID 59312961, compound

HRID 2171492Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[NH2:10][CH:11]([CH3:21])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)(O)[O-].[K+]>CN(C=O)C.O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:10][CH:11]([CH3:21])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[N:3][CH:4]=1)#[N:9]

Participants

Conditions

Temperature: 90 °C

Procedure

2-Chloro-5-cyanopyridine (477 mg, 3.4 mmol), tert-butyl (2-aminopropyl)carbamate (300 mg, 1.7 mmol) and potassium bicarbonate (345 mg, 3.4 mmol) are dissolved in DMF (10 ml) and stirred at 90° C. under argon for 12 h. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3×75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. After removal of the solvent, the residue is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1). 265 mg (55% of theory) of the product are obtained as a solid.

Workup

extractionextracted with ethyl acetate (3×75 ml)
washThe combined organic phases are washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulphate
concentrationconcentrated
customAfter removal of the solvent
customthe residue is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1)
custom265 mg (55% of theory) of the product are obtained as a solid

Sources & evidence

ORD record: ord-04c3e7b488d748858bb392e3fc74cfe7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051323B2

Reaction notes

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