NADPH → HCID 70655613, compound

HRID 1972423Notes

Reaction equation

HRID 1972423 reaction equation
[F:1][C:2]([F:34])([F:33])[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][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[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]2CN2CCOCC2)=CC=1)(O)C.FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@@H]2CN2CCOCC2)=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:34][C:2]([F:1])([F:33])[C@@:3]([C:6]1[CH:7]=[CH:8][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:19])=[O:20])[CH2:14][C@H:13]2[CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:10][CH:11]=1)([OH:5])[CH3:4]

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582864HCID 66582864, compoundHCID 66582905HCID 66582905, compoundHCID 70655583HCID 70655583, compound

Product 1

HCID 70655613HCID 70655613, compound

Procedure

(2R)-1,1,1-trifluoro-2-(4-((2S)-2-(4-morpholinylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2R)-2-(4-morpholinylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2S)-2-(4-morpholinylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.89-7.86 (m, 1H), 7.65-7.63 (m, 1H), 7.46-7.41 (m, 2H), 7.27-7.24 (m, 1H), 6.93-6.89 (m, 2H), 4.09-4.03 (m, 1H), 3.99-3.94 (m, 1H), 3.79-3.72 (m, 1H), 3.60-3.55 (m, 4H), 3.50-3.41 (m, 1H), 3.25-3.12 (m, 1H), 2.78-2.71 (m, 1H), 2.68-2.46 (m, 4H), 2.37-2.30 (m, 2H), 2.28-2.21 (m, 1H), 1.67 (s, 3H). m/z (ESI, +ve ion) 519.8 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.230 μM; GK-GKRP EC50 (LC MS/MS)=0.355 μM.

Sources & evidence

ORD record
ord-e909718be961485c93733fbe59b9427f
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…