NADPH → HCID 70655292, compound

HRID 1972355Notes

Reaction equation

[CH:1]1([C@@:4]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)([OH:9])[C:5]([F:8])([F:7])[F:6])[CH2:3][CH2:2]1.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>>[CH:1]1([C@:4]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:17][CH2:18][N:19]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[CH2:20][CH2:21]3)=[CH:14][CH:15]=2)([OH:9])[C:5]([F:7])([F:6])[F:8])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 5884NADPH

HCID 66582843HCID 66582843, compound

Product 1

HCID 70655292HCID 70655292, compound

Procedure

(1S)-1-cyclopropyl-2,2,2-trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanol. 1H NMR (400 MHz, CD3OD) δ 7.88-7.78 (m, 2H), 7.74-7.57 (m, 3H), 7.48 (s, 2H), 6.96-6.83 (m, 2H), 3.28-3.23 (m, 4H), 3.18-3.05 (m, 4H), 1.61-1.48 (m, 1H), 0.76-0.63 (m, 1H), 0.58-0.46 (m, 1H), 0.44-0.34 (m, 1H), 0.30-0.20 (m, 1H). m/z (ESI, +ve ion) 441.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=2.62 μM; GK-GKRP EC50 (LC MS/MS)=2.77 μM.

Sources & evidence

ORD record: ord-c1f71e989e5e4662821f7675267bfbad
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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