N-(dipropylcarbamothioyl)-3,4,5-trimethoxybenzamide → 2-(4-(4-((6-Amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

HRID 1972467Notes

Reaction equation

HRID 1972467 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C@@:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.NC1N=CC(S(N2CCN(C3C=CC([C@](O)(C)C(F)(F)F)=CC=3)CC2)(=O)=O)=CC=1.CCCN(C(NC(C1C=C(OC)C(OC)=C(OC)C=1)=O)=S)CCC>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:29])([CH3:28])[C:24]([F:26])([F:27])[F:25])=[CH:21][CH:22]=3)[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 12357717N-(dipropylcarbamothioyl)-3,4,5-trimethoxybenzamideHCID 66582554(2S)-2-(4-(4-((6-amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanolHCID 66584917(2R)-2-(4-(4-((6-amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

Product 1

HCID 665823132-(4-(4-((6-Amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

Procedure

(2S)-2-(4-(4-((6-amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol and (2R)-2-(4-(4-((6-amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (400 MHz, CD3OD) δ=8.30 (d, J=2.2 Hz, 1H), 7.74 (dd, J=2.4, 8.9 Hz, 1H), 7.46 (d, J=8.8 Hz, 2H), 6.95 (d, J=9.0 Hz, 2H), 6.64 (d, J=9.0 Hz, 1H), 3.30-3.24 (m, 4H), 3.18-3.08 (m, 4H), 1.68 (s, 3H). m/z (ESI, +ve ion) 431.1 (M+H)+. GK-GKRP IC50 (Binding)=0.359 μM; GK-GKRP EC50 (LC MS/MS-2)=0.605 μM.

Sources & evidence

ORD record
ord-6d9c9b323eb74dedbd4b827540316284
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…