NADPH → (2R)-2-(4-((2R)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

https://huagongshe.com/reaction/1972412

Participants

Role	Name	HCID	Charge
Reactant	NADPH	HCID 5884	—
Reactant	(2R)-2-(4-((2S)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol	HCID 66582461	—
Reactant	(2S)-2-(4-((2S)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol	HCID 66582744	—
Reactant	(2S)-2-(4-((2R)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol	HCID 66582745	—
Product	(2R)-2-(4-((2R)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol	HCID 70655831	—

Reaction Steps

(2R)-2-(4-((2S)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2R)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2S)-2-((4,4-difluoro-1-piperidinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (400 MHz, DMSO-d6) δ 8.08-8.06 (dd, J=5.1, 1.1 Hz, 1H), 7.70-7.68 (dd, J=3.7, 1.1 Hz, 1H), 7.38-7.34 (d, J=9.2 Hz, 2H), 7.32-7.30 (m, 1H), 6.89-6.87 (d, J=9.2 Hz, 2H), 4.15-4.11 (m, 1H), 3.46-3.38 (m, 3H), 3.15-3.08 (m, 1H), 2.69-2.63 (m, 1H), 2.59-2.52 (m, 2H), 2.46-2.38 (m, 4H), 2.30-2.25 (m, 1H), 1.79-1.73 (m, 4H), 1.61 (s, 3H). m/z (ESI, +ve ion) 554.2 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=1.05 μM; GK-GKRP EC50 (LC MS/MS)=1.53 μM.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08431563B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-758b792787914f3e920ace7af24f86ca
Source note	uspto-grants-2013_04