NADPH → HCID 70655524, compound
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[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH2:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].FC(F)(F)[C@](C1C=CC(N2CCN(S(C3C=CC=CC=3)(=O)=O)C[C@H]2CC2CCOCC2)=CC=1)(O)C.FC(F)(F)[C@](C1C=CC(N2CCN(S(C3C=CC=CC=3)(=O)=O)C[C@@H]2CC2CCOCC2)=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[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:19])=[O:20])[CH2:14][C@H:13]2[CH2:27][CH:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)=[CH:8][CH:7]=1)([OH:5])[CH3:4]Participants
Procedure
(2R)-1,1,1-trifluoro-2-(4-((2S)-4-(phenylsulfonyl)-2-(tetrahydro-2H-pyran-4-ylmethyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2R)-4-(phenylsulfonyl)-2-(tetrahydro-2H-pyran-4-ylmethyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2S)-4-(phenylsulfonyl)-2-(tetrahydro-2H-pyran-4-ylmethyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.83 (s, 2H), 7.65 (s, 3H), 7.44 (d, J=8.8 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 4.06 (m, 1H), 3.92-3.82 (m, 2H), 3.80-3.72 (m, 1H), 3.67 (d, J=11.5 Hz, 1H), 3.47-3.37 (m, 1H), 3.31-3.19 (m, 1H), 2.65 (dd, J=3.1, 11.5 Hz, 1H), 2.51 (dt, J=3.6, 11.4 Hz, 1H), 1.83-1.73 (m, 1H), 1.68 (s, 4H), 1.60-1.49 (m, 2H), 1.40-1.03 (m, 5H). m/z (ESI, +ve ion) 513.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.785 μM; GK-GKRP EC50 (LC MS/MS)=0.572 μM.
Sources & evidence
- ORD record
- ord-e1f6dfa78c524f878d6a8ff79c78c94e
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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