NADPH → HCID 86670315, compound

HRID 1972394Notes

Reaction equation

[F:1][C:2]([F:37])([F:36])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)(=[O:23])=[O:22])[CH2:17][C@@H:16]2[CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].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:7][C:4]([F:5])([F:6])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)(=[O:23])=[O:22])[CH2:17][C@H:16]2[CH2:29][CH:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)=[CH:11][CH:10]=1)([OH:8])[C:2]([F:36])([F:1])[F:37]

Participants

Reactant 2

HCID 5884NADPH

HCID 76325584HCID 76325584, compound

Product 1

HCID 86670315HCID 86670315, compound

Procedure

1,1,1,3,3,3-hexafluoro-2-(4-((2S)-2-(tetrahydro-2H-pyran-4-ylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.89 (d, J=4.9 Hz, 1H), 7.70-7.61 (m, 1H), 7.55 (d, J=9.0 Hz, 2H), 7.31-7.23 (m, 1H), 6.96 (d, J=9.2 Hz, 2H), 4.18 (br. s., 1H), 3.95-3.64 (m, 4H), 3.60-3.44 (m, 1H), 3.40-3.23 (m, 2H), 2.70 (dd, J=2.9, 11.7 Hz, 1H), 2.57 (dt, J=3.6, 11.4 Hz, 1H), 1.86-1.65 (m, 2H), 1.65-1.38 (m, 3H), 1.38-1.08 (m, 3H). m/z (ESI, +ve ion) 573.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.169 μM; GK-GKRP EC50 (LC MS/MS)=0.281 μM.

Sources & evidence

ORD record: ord-e20a1483ac9148659cbbf3e424cbca71
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

Loading…