NADPH → HCID 70655547, compound

HRID 1972448Notes

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][CH2:13]2)=[C:8]([C:26]#[C:27][C:28]2([CH3:32])[CH2:31][O:30][CH2:29]2)[CH:7]=1)([OH:5])[CH3:4].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: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][CH2:13]2)=[C:8]([C:26]#[C:27][C:28]2([CH3:32])[CH2:31][O:30][CH2:29]2)[CH:7]=1)([OH:5])[CH3:4]

Participants

Reactant 2

HCID 5884NADPH

HCID 66583065HCID 66583065, compound

Product 1

HCID 70655547HCID 70655547, compound

Procedure

(2S)-1,1,1-trifluoro-2-(3-((3-methyl-3-oxetanyl)ethynyl)-4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.92 (dd, J=1.2, 5.1 Hz, 1H), 7.67 (dd, J=1.2, 3.7 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 7.50 (s, 1H), 7.29 (dd, J=3.8, 5.0 Hz, 1H), 7.01 (d, J=8.6 Hz, 1H), 4.76 (d, J=5.5 Hz, 2H), 4.48 (d, J=5.5 Hz, 2H), 3.31-3.25 (m, 4H), 3.25-3.15 (m, 4H), 1.71-1.67 (m, 3H), 1.64 (s, 3H). m/z (ESI, +ve ion) 515.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=2.90 μM; GK-GKRP EC50 (LC MS/MS)=2.80 μM.

Sources & evidence

ORD record: ord-a9ece4a14a294d83bcfc6953612d17ca
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

Loading…