NADPH → (3R)-1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol

HRID 1972416Notes

Reaction equation

HRID 1972416 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C@@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C@H:11]([CH2:28][N:29]2[CH2:33][CH2:32][C@@H:31]([OH:34])[CH2:30]2)[CH2:10]1)(=[O:8])=[O:7].S1C=CC=C1S(N1CCN(C2C=CC([C@](O)(C)C(F)(F)F)=CC=2)[C@@H](CN2CC[C@@H](O)C2)C1)(=O)=O.S1C=CC=C1S(N1CCN(C2C=CC([C@@](O)(C)C(F)(F)F)=CC=2)[C@@H](CN2CC[C@@H](O)C2)C1)(=O)=O.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>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([C@:21]([OH:27])([CH3:26])[C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=2)[C@H:11]([CH2:28][N:29]2[CH2:33][CH2:32][C@@H:31]([OH:34])[CH2:30]2)[CH2:10]1)(=[O:7])=[O:8]

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582486HCID 66582486, compoundHCID 66586151(3R)-1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinolHCID 70655502HCID 70655502, compound

Product 1

HCID 66586150(3R)-1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol

Procedure

(3R)-1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol; (3R)-1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol; (3R)-1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol. 1H NMR (400 MHz, DMSO-d6) δ 8.07-8.05 (m, 1H), 7.69-7.67 (m, 1H), 7.38-7.36 (d, J=9.1 Hz, 2H), 7.32-7.29 (m, 1H), 6.90-6.86 (d, J=9.1 Hz, 2H), 4.71-4.67 (m, 1H), 4.17-4.12 (m, 3H), 3.46-3.41 (m, 2H), 3.17-3.04 (m, 1H), 2.99-3.92 (m, 2H), 2.63-2.59 (m, 1H), 2.48-2.38 (m, 3H), 1.95-1.89 (m, 2H), 1.61 (s, 3H), 1.55-1.50 (m, 1H). m/z (ESI, +ve ion) 520.1 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=3.50 μM.

Sources & evidence

ORD record
ord-6e0ca9386a3f44be8cdf0bf70d1d78c2
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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