NADPH → HCID 66582544, compound

HRID 1972410Notes

Reaction equation

HRID 1972410 reaction equation
[CH3:1][C:2]1([CH3:36])[O:7][CH2:6][CH2:5][N:4]([CH2:8][C@H:9]2[CH2:14][N:13]([S:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)(=[O:17])=[O:16])[CH2:12][CH2:11][N:10]2[C:23]2[CH:28]=[CH:27][C:26]([C@:29]([OH:35])([CH3:34])[C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)[CH2:3]1.CC1(C)OCCN(C[C@@H]2CN(S(C3SC=CC=3)(=O)=O)CCN2C2C=CC([C@@](O)(C)C(F)(F)F)=CC=2)C1.CC1(C)OCCN(C[C@H]2CN(S(C3SC=CC=3)(=O)=O)CCN2C2C=CC([C@@](O)(C)C(F)(F)F)=CC=2)C1.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>>[CH3:1][C:2]1([CH3:36])[O:7][CH2:6][CH2:5][N:4]([CH2:8][C@@H:9]2[CH2:14][N:13]([S:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)(=[O:17])=[O:16])[CH2:12][CH2:11][N:10]2[C:23]2[CH:28]=[CH:27][C:26]([C@:29]([OH:35])([CH3:34])[C:30]([F:31])([F:32])[F:33])=[CH:25][CH:24]=2)[CH2:3]1

Participants

5

Reactant 4

HCID 5884NADPHHCID 66582423HCID 66582423, compoundHCID 66582424HCID 66582424, compoundHCID 66582426HCID 66582426, compound

Product 1

HCID 66582544HCID 66582544, compound

Procedure

(2R)-2-(4-((2S)-2-((2,2-dimethyl-4-morpholinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2R)-2-((2,2-dimethyl-4-morpholinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol; (2S)-2-(4-((2S)-2-((2,2-dimethyl-4-morpholinyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol. 1H NMR (400 MHz, DMSO-d6) δ 8.07-8.05 (m, 1H), 7.68-7.66 (m, 1H), 7.37-7.35 (m, 2H), 7.32-7.29 (m, 1H), 6.88-6.86 (m, 2H), 4.15-4.12 (m, 1H), 3.91-3.88 (m, 1H), 3.46-3.42 (m, 4H), 3.13-3.07 (m, 1H), 2.60-2.55 (m, 1H), 2.49-2.38 (m, 3H), 2.27-2.22 (m, 1H), 2.16-2.05 (m, 3H), 1.61 (s, 3H), 1.11 (s, 3H), 1.07 (s, 3H). m/z (ESI, +ve ion) 548.2 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.182 μM; GK-GKRP EC50 (LC MS/MS)=0.295 μM.

Sources & evidence

ORD record
ord-92dc1c54d43441c2bbe4d547e66e6cb3
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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