5,7-Dichloroindoline → 5-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-(1-ethyl-3-methoxypropyl)-2(1H)-pyrazinone

HRID 2250999Notes

Reaction equation

HRID 2250999 reaction equation
Cl[C:2]1[C:3](=[O:16])[N:4]([CH:9]([CH2:14][CH3:15])[CH2:10][CH2:11][O:12][CH3:13])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[C:25]([Cl:27])[CH:26]=1)[NH:23][CH2:22][CH2:21]2>>[Cl:8][C:6]1[N:7]=[C:2]([N:23]2[C:24]3[C:20](=[CH:19][C:18]([Cl:17])=[CH:26][C:25]=3[Cl:27])[CH2:21][CH2:22]2)[C:3](=[O:16])[N:4]([CH:9]([CH2:14][CH3:15])[CH2:10][CH2:11][O:12][CH3:13])[CH:5]=1

Participants

3

Reactant 2

HCID 124822955,7-DichloroindolineHCID 184527953,5-dichloro-1-(1-ethyl-3-methoxypropyl)-2(1H)-pyrazinone

Product 1

HCID 101366925-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-(1-ethyl-3-methoxypropyl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-(1-ethyl-3-methoxypropyl)-2(1H)-pyrazinone and 5,7-dichloroindoline as the starting materials. mp 95-97° C.; 1H NMR (300 MHz, CDCl3): δ 7.16 (d, J=2.2 Hz, 1 H), 7.09 (d, J=1.8 Hz, 1 H), 6.78 (s, 1 H), 4.89-4.82 (m, 1 H), 4.32 (t, J=8.1 Hz, 2 H), 3.39-3.27 (m, 2 H), 3.25 (s, 3 H), 3.11 (t, J=7.9 Hz, 2 H), 2.01-1.93 (m, 2 H), 1.84-1.72 (m, 2 H), 0.86 (t, J=7.5 Hz, 3 H); HRMS (ESI) calcd for C18H21N3O2Cl3 (M+H)+: 416.0699; found m/z 416.0717.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-3e49f8b77a834f6c99030e9b41e672ac
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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