Tetrahydrothiopyran-4-one → n-(2-Oxo-2-{[1-(tetrahydro-2h-thiopyran-4-yl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

HRID 564404Notes

Reaction equation

HRID 564404 reaction equation
C(O[C@@H:5]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14]O[CH2:12][CH2:11]2)[CH2:7][C@H:6]1[NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)C=C.[S:33]1CCC(=O)CC1.O1CCC(=O)CC1>>[O:32]=[C:17]([NH:16][CH:6]1[CH2:5][CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][S:33][CH2:12][CH2:11]2)[CH2:7]1)[CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1

Participants

4

Reactant 3

HCID 66173Tetrahydrothiopyran-4-oneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 67005152Rel-n-(2-{[(3r,4r)-4-(allyloxy)-1-(tetrahydro-2h-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 67005295n-(2-Oxo-2-{[1-(tetrahydro-2h-thiopyran-4-yl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

Procedure

The title compound was synthesized in similar fashion to rel-N-(2-{[(3R,4R)-4-(allyloxy)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide, tetrahydro-4H-thiopyran-4-one was substituted for tetrahydro-4H-pyran-4-one and was isolated as a white solid. 1H-NMR (DMSO) δ: 1.48-1.60 (m, 2H), 1.90-2.50 (m, 8H), 2.60-2.70 (m, 2H), 2.79-2.96 (m, 2×), 3.70-4.05 (m, 6H), 5.05-5.25 (m, 2H), 5.75-5.95 (m, 1H), 7.70 (t, J=8.2 Hz, 1H), 7.93 (d, J=8.2 Hz, 1H), 8.18 (m, 2H), 9.00 (m, 1H). MS m/z: 472 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-a8b026b76cab4e2b8a9644377b9beef3
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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