NADPH → HCID 66582320, compound

HRID 1972350Notes

Reaction equation

HRID 1972350 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C@@H:9]1[CH2:14][N:13]([S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])=[O:16])[CH2:12][CH2:11][N:10]1[C:23]1[CH:28]=[CH:27][C:26]([C@@:29]([OH:35])([CH3:34])[C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1.ClC1C=CC(Cl)=CC=1[C@H]1CN(S(C2SC=CC=2)(=O)=O)CCN1C1C=CC([C@](O)(C)C(F)(F)F)=CC=1.ClC1C=CC(Cl)=CC=1[C@@H]1CN(S(C2SC=CC=2)(=O)=O)CCN1C1C=CC([C@](O)(C)C(F)(F)F)=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>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C@H:9]1[CH2:14][N:13]([S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:17])[CH2:12][CH2:11][N:10]1[C:23]1[CH:28]=[CH:27][C:26]([C@@:29]([OH:35])([CH3:34])[C:30]([F:32])([F:31])[F:33])=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582353HCID 66582353, compoundHCID 66582407HCID 66582407, compoundHCID 66582591HCID 66582591, compound

Product 1

HCID 66582320HCID 66582320, compound

Procedure

(2S)-2-(4-((2R)-2-(2,5-dichlorophenyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2R)-2-(4-((2S)-2-(2,5-dichlorophenyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2R)-2-(4-((2R)-2-(2,5-dichlorophenyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (300 MHz, CDCl3) δ 7.63 (d, J=5.0 Hz, 1H), 7.55 (dd, J=3.65, 1.0 Hz, 1H), 7.36 (d, J=8.5 Hz, 2H), 7.29 (d, J=1.8 Hz, 1H), 7.24 (s, 1H), 7.14 (dd, J=4.9, 3.9 Hz, 1H), 7.08 (dd, J=8.5, 2.5 Hz, 1H), 6.85 (d, J=8 62 Hz, 2H), 4.84 (dd, J=9.0, 3.4 Hz, 1H), 3.73-3.90 (m, 2H), 3.60 (d, J=12.3 Hz, 1H), 3.19-3.31 (m, 1H), 3.00-3.11 (m, 1H), 2.59-2.71 (m, 1H), 1.68 (d, J=3.5 Hz, 3H). m/z (ESI, +ve ion) 586.8 (M+Na)+. GK-GKRP EC50 (NADPH-coupled)=2.64 μM; GK-GKRP EC50 (LC MS/MS)=1.96 μM.

Sources & evidence

ORD record
ord-dd99212552d2444ca97f2090ae925654
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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