NADPH → HCID 86670320, compound

HRID 1972400Notes

Reaction equation

[ClH:1].[F:2][C:3]([F:39])([F:38])[C:4]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)(=[O:24])=[O:23])[CH2:18][C@H:17]2[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)=[CH:12][CH:11]=1)([OH:9])[C:5]([F:8])([F:7])[F:6].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>>[ClH:1].[F:8][C:5]([F:6])([F:7])[C:4]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)(=[O:23])=[O:24])[CH2:18][C@@H:17]2[CH2:30][C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)=[CH:12][CH:11]=1)([OH:9])[C:3]([F:39])([F:38])[F:2]

Participants

Reactant 2

HCID 5884NADPH

HCID 86670322HCID 86670322, compound

Product 1

HCID 86670320HCID 86670320, compound

Procedure

1,1,1,3,3,3-hexafluoro-2-(4-((2R)-2-(4-methylbenzyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol hydrochloride. 1H NMR (400 MHz, CD3OD) δ 7.86-7.83 (m, 1H), 7.61-7.56 (m, 3H), 7.24-7.20 (m, 1H), 7.13-7.07 (m, 4H), 7.05-7.00 (m, 2H), 4.15-4.08 (m, 1H), 3.86-3.81 (m, 1H), 3.66-3.55 (m, 2H), 3.41-3.33 (m, 1H), 3.10-3.03 (m, 1H), 2.61-2.53 (m, 2H), 2.51-2.46 (m, 1H), 2.29 (s, 3H). m/z (ESI, +ve ion) 578.8 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=2.50 μM; GK-GKRP EC50 (LC MS/MS)=2.62 μM.

Sources & evidence

ORD record: ord-f2c67d2cb1fe4286b816e64567d1da64
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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