NADPH → HCID 70655495, compound

HRID 1972376Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[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[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH3:27])=[CH:8][CH:7]=1)([OH:5])[CH3:4].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:29][C:2]([F:1])([F:28])[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[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH3:27])=[CH:8][CH:7]=1)([OH:5])[CH3:4]

Participants

Reactant 2

HCID 5884NADPH

HCID 66586149HCID 66586149, compound

Product 1

HCID 70655495HCID 70655495, compound

Procedure

(2S)-1,1,1-trifluoro-2-(4-((2S)-2-methyl-4-(phenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (300 MHz, MeOH) δ 7.72 (d, J=7.3 Hz, 2H), 7.62-7.50 (m, 3H), 7.35 (d, J=8.5 Hz, 2H), 6.81 (d, J=8.6 Hz, 2H), 3.51 (d, J=11.6 Hz, 1H), 3.34-3.26 (m, 3H), 3.15-3.01 (m, 1H), 2.69 (d, J=11.4 Hz, 1H), 2.53 (t, J=8.9 Hz, 1H), 1.57 (s, 3H), 0.98 (d, J=6.4 Hz, 3H). m/z (ESI, +ve ion) 429.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=3.12 μM; GK-GKRP EC50 (LC MS/MS)=4.01 μM

Sources & evidence

ORD record: ord-16da478884cc4676a41771a1d78542bc
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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