N-(dipropylcarbamothioyl)-3,4,5-trimethoxybenzamide → (2S)-2-(4-(4-((5-amino-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

HRID 1972463Notes

Reaction equation

HRID 1972463 reaction equation
[NH2:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C@:22]([OH:28])([CH3:27])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.CCCN(C(NC(C1C=C(OC)C(OC)=C(OC)C=1)=O)=S)CCC>>[NH2:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[CH:18][C:19]([C@@:22]([OH:28])([CH3:27])[C:23]([F:26])([F:25])[F:24])=[CH:20][CH:21]=3)[CH2:14][CH2:15]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 12357717N-(dipropylcarbamothioyl)-3,4,5-trimethoxybenzamideHCID 66582429(2R)-2-(4-(4-((5-amino-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

Product 1

HCID 66582809(2S)-2-(4-(4-((5-amino-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

Procedure

(2R)-2-(4-(4-((5-amino-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (400 MHz, CD3OD) δ=7.48 (d, J=8.8 Hz, 2H), 7.23 (d, J=4.1 Hz, 1H), 7.03-6.91 (m, 2H), 6.08 (d, J=4.1 Hz, 1H), 3.32-3.27 (m, 4H), 3.21-3.15 (m, 4H), 1.70 (s, 3H). m/z (ESI, +ve ion) 436.0 (M+H)+. GK-GKRP IC50 (Binding)=0.448 μM; GK-GKRP EC50 (LC MS/MS-2)=0.836 μM.

Sources & evidence

ORD record
ord-3ee94a780c6842caa8e3df794ce8a0ef
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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