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

HRID 1271142Notes

Reaction equation

HRID 1271142 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.[Cl:15][C:16]1[CH:17]=[C:18]([O:25][CH3:26])[CH:19]=[C:20]2[C:24]=1[NH:23][CH2:22][CH2:21]2>>[Cl:11][C:9]1[N:8]=[C:7]([N:23]2[C:24]3[C:20](=[CH:19][C:18]([O:25][CH3:26])=[CH:17][C:16]=3[Cl:15])[CH2:21][CH2:22]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 184528197-Chloro-5-methoxyindoline hydrochloride

Product 1

HCID 102703665-Chloro-3-(7-chloro-5-methoxy-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 7-chloro-5-methoxyindoline hydrochloride as the starting materials. mp 143–145° C.; 1H NMR (300 MHz, CDCl3): δ 6.89 (s, 1 H), 6.77–6.72 (m, 2 H), 4.96–4.89 (m, 1 H), 4.34 (t, J=7.9 Hz, 2 H), 3.76 (s, 3 H), 3.07 (t, J=7.7 Hz, 2 H), 1.74–1.64 (m, 2 H), 1.33 (d, J=7.0 Hz, 3 H), 0.89 (t, J=7.6 Hz, 3 H); HRMS (ESI) calcd for C17H20N3O2Cl2 (M+H)+: 368.0933; found m/z 368.0927.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-34dd954f433546ee9f61f02dc6c23948
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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