Water → HCID 18936665, compound

HRID 357062

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[NH:16]1[CH2:22][C:20](=[O:21])[NH:19][C:17]1=[O:18].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[N:15]1[CH:14]=[CH:13][N:12]2[C:7]([S:6][CH2:5][CH2:4][CH2:3][CH2:2][N:19]3[C:20](=[O:21])[CH2:22][NH:16][C:17]3=[O:18])=[CH:8][CH:9]=[CH:10][C:11]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2.41 g (10.0 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 1.00 g (10.0 mmol) of hydantoin in 30 ml of N,N-dimethylformamide, 1.50 ml (10.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by stirring at 80° C. for 16 hours. After the reaction mixture was cooled, water was added; the mixture was extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=20/1→10/1) to yield 1.27 g (41.7%, yellow solid) of the desired product.

Workup

temperatureAfter the reaction mixture was cooled
extractionthe mixture was extracted with ethyl acetate
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent, chloroform/methanol=20/1→10/1)

Sources & evidence

ORD record: ord-356bb265275d412ca0d7a303c808ed76
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Linked notes

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