NADPH → HCID 86670313, compound

HRID 1972385Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[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][N:25]=3)(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].C1N=C(N)C2N=CN([C@@H]3[O:41][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:1][C:2]([F:27])([F:26])[C:3]([OH:41])=[O:5].[F:27][C:2]([F:1])([F:26])[C@:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][N:25]=3)(=[O:20])=[O:19])[CH2:16][CH2:17]2)=[CH:8][CH:7]=1)([OH:5])[CH3:4]

Participants

Reactant 2

HCID 5884NADPH

HCID 70655443HCID 70655443, compound

Product 1

HCID 86670313HCID 86670313, compound

Procedure

(2R)-1,1,1-trifluoro-2-(4-(4-(1,3-thiazol-2-ylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=3.1 Hz, 1H), 7.67 (d, J=3.1 Hz, 1H), 7.48 (d, J=8.8 Hz, 2H), 6.94 (d, J=9.0 Hz, 2H), 3.48-3.58 (m, 4H), 3.27-3.38 (m, 4H), 1.76 (s, 3H). m/z (ESI, +ve ion) 421.8 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=1.18 μM; GK-GKRP EC50 (LC MS/MS)=4.75 μM.

Sources & evidence

ORD record: ord-61939039baf3418f93547e9f1f05c717
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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