NADPH → HCID 66584065, compound

HRID 1972415Notes

Reaction equation

HRID 1972415 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C@@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C@H:11]([CH2:28][C:29]#[N:30])[CH2:10]1)(=[O:8])=[O:7].S1C=CC=C1S(N1CCN(C2C=CC([C@](O)(C)C(F)(F)F)=CC=2)[C@@H](CC#N)C1)(=O)=O.S1C=CC=C1S(N1CCN(C2C=CC([C@@](O)(C)C(F)(F)F)=CC=2)[C@@H](CC#N)C1)(=O)=O.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>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([C@:21]([OH:27])([CH3:26])[C:22]([F:24])([F:23])[F:25])=[CH:19][CH:20]=2)[C@H:11]([CH2:28][C:29]#[N:30])[CH2:10]1)(=[O:7])=[O:8]

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582406HCID 66582406, compoundHCID 66582457HCID 66582457, compoundHCID 66582489HCID 66582489, compound

Product 1

HCID 66584065HCID 66584065, compound

Procedure

((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)acetonitrile; ((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)acetonitrile; ((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)acetonitrile. 1H NMR (400 MHz, CDCl3) δ 7.68-7.66 (m, 1H), 7.62-7.60 (m, 1H), 7.48-7.46 (d, J=8.8 Hz, 2H), 7.19-7.17 (m, 1H), 6.87-6.85 (d, J=8.8 Hz, 2H), 4.11-4.04 (m, 2H), 3.89-3.78 (m, 2H), 3.48-3.41 (m, 2H), 3.27-3.20 (m, 1H), 2.77-2.72 (m, 1H), 2.69-2.61 (m, 1H), 1.74 (s, 3H). m/z (ESI, +ve ion) 460.1 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=3.03 μM; GK-GKRP EC50 (LC MS/MS)=3.94 μM.

Sources & evidence

ORD record
ord-254cba035c8d44eca08776396e7acc83
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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