NADPH → HCID 66582381, compound

HRID 1972424Notes

Reaction equation

HRID 1972424 reaction equation
[CH2:1]([N:8]([CH2:10][C@H:11]1[CH2:16][N:15]([S:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)(=[O:19])=[O:18])[CH2:14][CH2:13][N:12]1[C:25]1[CH:30]=[CH:29][C:28]([C@:31]([OH:37])([CH3:36])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C[C@@H]1CN(S(C2SC=CC=2)(=O)=O)CCN1C1C=CC([C@@](O)(C)C(F)(F)F)=CC=1)C)C1C=CC=CC=1.C(N(C[C@H]1CN(S(C2SC=CC=2)(=O)=O)CCN1C1C=CC([C@@](O)(C)C(F)(F)F)=CC=1)C)C1C=CC=CC=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>>[CH2:1]([N:8]([CH2:10][C@@H:11]1[CH2:16][N:15]([S:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)(=[O:19])=[O:18])[CH2:14][CH2:13][N:12]1[C:25]1[CH:26]=[CH:27][C:28]([C@:31]([OH:37])([CH3:36])[C:32]([F:34])([F:33])[F:35])=[CH:29][CH:30]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582572HCID 66582572, compoundHCID 66582755HCID 66582755, compoundHCID 66582856HCID 66582856, compound

Product 1

HCID 66582381HCID 66582381, compound

Procedure

(2R)-2-(4-((2S)-2-((benzyl(methyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2R)-2-((benzyl(methyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2S)-2-((benzyl(methyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.88-7.86 (m, 1H), 7.66-7.64 (m, 1H), 7.44-7.40 (m, 2H), 7.31-7.21 (m, 6H), 6.86-6.82 (m, 2H), 4.08-3.97 (m, 2H), 3.72-3.66 (m, 1H), 3.53-3.45 (m, 2H), 3.43-3.37 (m, 1H), 3.19-3.11 (m, 1H), 2.95-2.87 (m, 1H), 2.70-2.65 (m, 1H), 2.62-2.54 (m, 1H), 2.25-2.19 (m, 1H), 2.17 (s, 3H), 1.67 (s, 3H). m/z (ESI, +ve ion) 553.8 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=1.01 μM; GK-GKRP EC50 (LC MS/MS)=1.22 μM.

Sources & evidence

ORD record
ord-b1d3785f3a814158bfa9f0c5a782ecbb
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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