HCID 45381772, compound → HCID 45381771, compound

HRID 2176168Notes

Reaction equation

HRID 2176168 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[N:10]2[C:18]3[CH:17]=[CH:16][C:15]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:11]2=3)[CH2:26][CH2:25]4)=[CH:4][CH:3]=1>CO.[Pt]=O>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:14][C:13]=3[C:12]3[CH2:23][N:24]4[CH2:25][CH2:26][CH:27]([C:11]2=3)[CH2:28][CH2:29]4)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 45381772HCID 45381772, compound

Product 1

HCID 45381771HCID 45381771, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 6-[(Z)-2-(6-methylpyridin-3-yl)vinyl]-9-(methylsulfonyl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (20 mg, 0.049 mmol; Example 181) in methanol was treated with platinum oxide under a hydrogen atmosphere (1 atm) at 40° C. for 16 hours to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.62-1.76 (m, 2H), 1.90-2.05 (m, 2H), 2.40 (s, 3H), 2.91-3.24 (m, 10H), 4.26 (s, 2H), 4.49 (t, J=6 Hz, 2H), 7.11 (d, J=8 Hz, 1H), 7.34 (dd, J=8, 2 Hz, 1H), 7.42 (d, J=9 Hz, 1H), 7.59 (dd, J=9, 2 Hz, 1H), 7.84 (d, J=2 Hz, 1H), 7.95 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 410 (M+H)+.

Sources & evidence

ORD record
ord-cbd4c8999c2d4e52b5248657d66345d1
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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