NADPH → HCID 66582528, compound

HRID 1972388Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C@:22]([OH:28])([CH3:27])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[C@@H:12]([CH3:29])[CH2:11]2)(=[O:9])=[O:8])=[N:4][N:3]=1.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>>[NH2:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C@@:22]([OH:28])([CH3:27])[C:23]([F:25])([F:26])[F:24])=[CH:18][CH:17]=3)[C@@H:12]([CH3:29])[CH2:11]2)(=[O:8])=[O:9])=[N:4][N:3]=1

Participants

Reactant 2

HCID 5884NADPH

HCID 70655536HCID 70655536, compound

Product 1

HCID 66582528HCID 66582528, compound

Procedure

(2R)-2-(4-((2S)-4-((5-amino-1,3,4-thiadiazol-2-yl)sulfonyl)-2-methyl-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (400 MHz, CD3OD) δ 7.47 (d, J=8.6 Hz, 2H), 6.98 (d, J=8.6 Hz, 2H), 4.10-4.03 (m, 1H), 3.80-3.74 (m, 1H), 3.57-3.51 (m, 1H), 3.42-3.36 (m, 1H), 3.29-3.17 (m, 2H), 3.15-3.07 (m, 1H), 1.68 (s, 3H), 1.10-1.06 (d, J=6.5 Hz, 3H). m/z (ESI, +ve ion) 452.1 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=3.04 μM; GK-GKRP EC50 (LC MS/MS)=5.62 μM.

Sources & evidence

ORD record: ord-5d7fff974589433e933630f52987457f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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