Potassium Carbonate → HCID 86760665, compound

HRID 2222899Notes

Reaction equation

[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2].C(=O)([O-])[O-].[K+].[K+].[SH:30][CH2:31][CH2:32][CH2:33][OH:34]>CN(C)C=O>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:30][CH2:31][CH2:32][CH2:33][OH:34])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

trans-N-Cyanomethyl-2-(4-fluorobenzenesulfonylmethyl)-cyclohexanecarboxamide (101 mg) and potassium carbonate (73 mg) were weighed into a 5 mL vial fitted with a stir bar and cap. Dimethylformamide (1 mL) and 3-mercapto-1-propanol (45 μL) were added. The vial was flushed with nitrogen and sealed with a cap. After stirring the reaction mixture at 100° C. for 6 h, the reaction mixture was allowed to cool to room temperature and stirred overnight. The reaction mixture was diluted with acetonitrile (4 mL) and filtered to remove solids. Concentration of the filtrate followed by chromatography of the crude residue on C-18 reverse-phase HPLC provided the desired product as a white solid. 1H NMR (DMSO-d6): δ=8.56 (1H, t), 7.68 (2H, m), 7.46 (2H, m), 4.05 (2H, d), 3.49 (2H, t), 3.14 (3H, m), 2.92 (1H, d), 2.2 (1H, m), 2.0 (2H, m), 1.8 (2H, m), 1.7 (3H, m), 1.3 (1H, m), 1.13 (3H, m). MS [ESI, (M−H)−] m/z=409.3 amu

Workup

customvial fitted with a stir bar
customcap
customThe vial was flushed with nitrogen
customsealed with a cap
temperatureto cool to room temperature
stirringstirred overnight
additionThe reaction mixture was diluted with acetonitrile (4 mL)
filtrationfiltered
customto remove solids

Sources & evidence

ORD record: ord-38f202ff677d42fa8a51074eeca94e97
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371747B2

Reaction notes

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