3,5-dichloro-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone → 5-Chloro-3-(5-methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone

HRID 2251039Notes

Reaction equation

HRID 2251039 reaction equation
Cl[C:2]1[C:3](=[O:13])[N:4]([CH2:9][CH2:10][S:11][CH3:12])[CH:5]=[C:6]([Cl:8])[N:7]=1.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:8][C:6]1[N:7]=[C:2]([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:3](=[O:13])[N:4]([CH2:9][CH2:10][S:11][CH3:12])[CH:5]=1

Participants

3

Reactant 2

HCID 184528023,5-dichloro-1-[2-(methylthio)ethyl]-2(1H)-pyrazinoneHCID 18452815HCID 18452815, compound

Product 1

HCID 101557555-Chloro-3-(5-methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone and 5-methoxy-7-methylindoline hydrochloride as the starting materials. mp 111-113° C.; 1H NMR (300 MHz, CDCl3): δ 6.80 (s, 1 H), 6.68 (d, J=2.2 Hz, 1 H), 6.59 (d, J=2.2 Hz, 1 H), 4.40 (t, J=7.7 Hz, 2 H), 4.04 (t, J=7.1 Hz, 2 H), 3.79 (s, 3 H), 3.04 (t, J=7.7 Hz, 2 H), 2.89 (t, J=7.2 Hz, 2 H), 2.18 (s, 3 H), 2.06 (s, 3 H); HRMS (CI) calcd for C17H20N3O2SCl (M+): 365.0965; found m/z 365.0967.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-3bf16d8c94fa412e8fd33f8e1b1aa4bb
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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