Tetrahydrothiopyran-4-one → HCID 178510425, compound

HRID 536932Notes

Reaction equation

HRID 536932 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)[CH:3]=1.[S:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1>CO.C(Cl)Cl>[C:18]1([C:4]2[CH:3]=[C:2]([C:27]3([OH:30])[CH2:28][CH2:29][S:24][CH2:25][CH2:26]3)[CH:7]=[CH:6][C:5]=2[NH:8][C:9]([C:11]2[NH:12][CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

4

Reactant 2

HCID 66173Tetrahydrothiopyran-4-oneHCID 178510376HCID 178510376, compound

Product 1

HCID 178510425HCID 178510425, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the procedure of Example 11 using 4-cyano-1H-imidazole-2-carboxylic acid (4-bromo-2-cyclohex-1-enyl-phenyl)-amide (as prepared in the previous step, 120 mg, 0.323 mmol) and tetrahydro-thiopyran-4-one (188 mg, 1.62 mmol). Silica gel chromatography (1-3% MeOH/DCM) afforded the title compound (82.3 mg, 62%) as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 12.56 (s, 1H), 9.66 (s, 1H), 8.29 (d, 1H, J=8.6 Hz), 7.74 (d, 1H, J=2.5 Hz), 7.42 (dd, 1H, J=8.6, 2.3 Hz), 7.33 (d, 1H, J=2.3 Hz), 5.86 (m, 1H), 3.22 (m, 2H), 2.46-2.54 (m, 2H), 2.22-2.33 (m, 4H), 2.16-2.22 (m, 2H), 2.01-2.09 (m, 2H), 1.73-1.89 (m, 5H). Mass spectrum (ESI, m/z): Calcd. for C22H24N4O2S, 409.2 (M+H). found 409.1.

Sources & evidence

ORD record
ord-4e82e064fb8e42dea8030cd46b142aa2
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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