NADPH → HCID 66582432, compound

HRID 1972418Notes

Reaction equation

HRID 1972418 reaction equation
[CH:1]1([CH2:7][C@H:8]2[CH2:13][N:12]([S:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)(=[O:16])=[O:15])[CH2:11][CH2:10][N:9]2[C:22]2[CH:27]=[CH:26][C:25]([C@:28]([OH:34])([CH3:33])[C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C[C@@H]2CN(S(C3SC=CC=3)(=O)=O)CCN2C2C=CC([C@@](O)(C)C(F)(F)F)=CC=2)CCCCC1.C1(C[C@H]2CN(S(C3SC=CC=3)(=O)=O)CCN2C2C=CC([C@@](O)(C)C(F)(F)F)=CC=2)CCCCC1.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([CH2:7][C@@H:8]2[CH2:13][N:12]([S:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)(=[O:16])=[O:15])[CH2:11][CH2:10][N:9]2[C:22]2[CH:23]=[CH:24][C:25]([C@:28]([OH:34])([CH3:33])[C:29]([F:30])([F:31])[F:32])=[CH:26][CH:27]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582621HCID 66582621, compoundHCID 66582815HCID 66582815, compoundHCID 70655569HCID 70655569, compound

Product 1

HCID 66582432HCID 66582432, compound

Procedure

(2R)-2-(4-((2S)-2-(cyclohexylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2R)-2-(cyclohexylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2S)-2-(cyclohexylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (400 MHz, CDCl3) δ 7.64-7.62 (m, 1H), 7.57-7.55 (m, 1H), 7.43-7.40 (d, J=8.6 Hz, 2H), 7.17-7.14 (m, 1H), 6.81-6.79 (d, J=8.6 Hz, 2H), 3.97-3.90 (m, 1H), 3.77-3.65 (m, 2H), 3.44-3.39 (m, 1H), 3.34-3.27 (m, 1H), 2.73-2.67 (m, 1H), 2.63-2.56 (m, 1H), 2.32-2.31 (m, 1H), 1.83-1.74 (m, 2H), 1.74 (s, 3H), 1.69-1.62 (m, 4H), 1.28-1.15 (m, 4H), 0.90-0.84 (m, 2H). m/z (ESI, +ve ion) 517.2 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=1.00 μM; GK-GKRP EC50 (LC MS/MS)=1.32 μM.

Sources & evidence

ORD record
ord-31ad7c817a2c419e993b358e913b9459
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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