5,7-Dichloroindoline → 5-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-[(1R)-1-(methoxymethyl)propyl]-2(1H)-pyrazinone

HRID 1271165Notes

Reaction equation

HRID 1271165 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4]([C@@H:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[C:24]([Cl:26])[CH:25]=1)[NH:22][CH2:21][CH2:20]2>>[Cl:8][C:6]1[N:7]=[C:2]([N:22]2[C:23]3[C:19](=[CH:18][C:17]([Cl:16])=[CH:25][C:24]=3[Cl:26])[CH2:20][CH2:21]2)[C:3](=[O:15])[N:4]([C@@H:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 124822955,7-DichloroindolineHCID 44189755HCID 44189755, compound

Product 1

HCID 101117505-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-[(1R)-1-(methoxymethyl)propyl]-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[(1R)-1-(methoxymethyl)propyl]-2(1H)-pyrazinone and 5,7-dichloroindoline as the starting materials. mp 143–146° C.; 1H NMR (300 MHz, CDCl3): δ 7.15 (d, J=1.8 Hz, 1 H), 7.09 (d, J=1.8 Hz, 1 H), 7.03 (s, 1 H), 4.94–4.90 (m, 1 H), 4.32 (t, J=8.1 Hz, 2 H), 3.65 (dd, J=10.6, 5.5 Hz, 1 H), 3.54 (dd, J=10.7, 3.3 Hz, 1 H), 3.33 (s, 3 H), 3.10 (t, J=8.1 Hz, 2 H), 1.88–1.70 (m, 2 H), 0.91 (t, J=7.3 Hz, 3 H); HRMS (ESI) calcd for C17H19N3O2Cl3 (M+H)+: 402.0543; found m/z 402.0568.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-20f5850678554839a07fcf05e9f961f8
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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