NADPH → HCID 70655293, compound

HRID 1972395Notes

Reaction equation

HRID 1972395 reaction equation
[F:1][C:2]([F:35])([F:34])[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][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])=[CH:8][CH:7]=1)([OH:5])[CH3:4].FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@H]2CC2C=CC=CC=2F)=CC=1)(O)C.FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@@H]2CC2C=CC=CC=2F)=CC=1)(O)C.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>>[F:35][C:2]([F:1])([F:34])[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][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@H:13]2[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])=[CH:8][CH:7]=1)([OH:5])[CH3:4]

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582644HCID 66582644, compoundHCID 66586137HCID 66586137, compoundHCID 70655591HCID 70655591, compound

Product 1

HCID 70655293HCID 70655293, compound

Procedure

(2R)-1,1,1-trifluoro-2-(4-((2S)-2-(2-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2R)-2-(2-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2S)-2-(2-fluorobenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.86 (d, J=4.9 Hz, 1H), 7.64-7.54 (m, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.32 (t, J=7.6 Hz, 1H), 7.26-7.16 (m, 2H), 7.14-6.93 (m, 4H), 4.29-4.18 (m, 1H), 3.87-3.76 (m, 1H), 3.61-3.48 (m, 2H), 3.41 (dt, J=3.5, 12.0 Hz, 1H), 3.13-3.01 (m, 1H), 2.85 (dd, J=3.8, 13.2 Hz, 1H), 2.62-2.49 (m, 2H), 1.69 (s, 3H). m/z (ESI, +ve ion) 529.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.515 μM; GK-GKRP EC50 (LC MS/MS)=0.850 μM.

Sources & evidence

ORD record
ord-5f216d85147d46d58d058efbdec86cec
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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