NADPH → (2R)-1,1,1-trifluoro-2-(4-((2R)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

HRID 1972397Notes

Reaction equation

[F:1][C:2]([F:35])([F:34])[C@@:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@H]2CC2C=CC(F)=CC=2)=CC=1)(O)C.FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@@H]2CC2C=CC(F)=CC=2)=CC=1)(O)C.C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O)C=2N=1>>[F:35][C:2]([F:1])([F:34])[C@@:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@H:13]2[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)=[CH:8][CH:7]=1)([OH:5])[CH3:4]

Participants

Reactant 4

HCID 5884NADPH

HCID 66582971(2S)-1,1,1-trifluoro-2-(4-((2S)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

HCID 66586184(2S)-1,1,1-trifluoro-2-(4-((2R)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

HCID 70655517(2R)-1,1,1-trifluoro-2-(4-((2S)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

Product 1

HCID 70654813(2R)-1,1,1-trifluoro-2-(4-((2R)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

Procedure

(2R)-1,1,1-trifluoro-2-(4-((2S)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2R)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2S)-2-(4-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.93-7.81 (m, 1H), 7.61 (d, J=2.5 Hz, 1H), 7.56-7.43 (m, 2H), 7.30-7.15 (m, 3H), 7.08-6.91 (m, 4H), 4.11 (br. s., 1H), 3.84 (d, J=11.0 Hz, 1H), 3.60 (d, J=11.3 Hz, 1H), 3.55-3.46 (m, 1H), 3.40-3.35 (m, 1H), 3.21-2.96 (m, 1H), 2.72-2.47 (m, 3H), 1.70 (s, 3H). m/z (ESI, +ve ion) 529.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.895 μM; GK-GKRP EC50 (LC MS/MS)=1.25 μM.

Sources & evidence

ORD record: ord-e011d092aeb149a28a70c1fadf61f0d8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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