3,5-dichloro-1-methylpropyl-2(1H)-pyrazinone → 5-Chloro-3-(5-methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-1-(1-methylpropyl)-2(1H)-pyrazinone

HRID 1271144Notes

Reaction equation

HRID 1271144 reaction equation
[CH:1]([N:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7](Cl)[C:6]1=[O:13])([CH2:3][CH3:4])[CH3:2].Cl.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[C:24]([CH3:26])[CH:25]=1)[NH:22][CH2:21][CH2:20]2>>[Cl:11][C:9]1[N:8]=[C:7]([N:22]2[C:23]3[C:19](=[CH:18][C:17]([O:16][CH3:15])=[CH:25][C:24]=3[CH3:26])[CH2:20][CH2:21]2)[C:6](=[O:13])[N:5]([CH:1]([CH3:2])[CH2:3][CH3:4])[CH:10]=1

Participants

3

Reactant 2

HCID 184527883,5-dichloro-1-methylpropyl-2(1H)-pyrazinoneHCID 18452815HCID 18452815, compound

Product 1

HCID 99681495-Chloro-3-(5-methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-1-(1-methylpropyl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 1-sec-butyl-3,5-dichloro-2(1H)-pyrazinone and 5-methoxy-7-methylindoline hydrochloride as the starting materials. mp 176–178° C.; 1H NMR (300 MHz, CDCl3): δ 6.70 (s, 1 H), 6.66 (d, J=2.2 Hz, 1 H), 6.57 (d, J=2.2 Hz, 1 H), 4.98–4.91 (m, 1 H), 4.38 (t, J=7.7 Hz, 2 H), 3.77 (s, 3 H), 3.02 (t, J=7.7 Hz, 2 H), 2.04 (s, 3 H), 1.74–1.64 (m, 2 H), 1.33 (d, J=6.9 Hz, 3 H), 0.90 (t, J=7.5 Hz, 3 H); HRMS (ESI) calcd for C18H23N3O2Cl (M+H)+: 348.1479; found m/z 348.1490.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-1aa2a1e9482a458786a7301c58ef25dc
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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