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

HRID 1271192Notes

Reaction equation

HRID 1271192 reaction equation
Cl[C:2]1[C:3](=[O:16])[N:4]([CH:9]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]([O:28][CH3:29])[CH:22]=[C:23]2[C:27]=1[NH:26][CH2:25][CH2:24]2>>[Cl:8][C:6]1[N:7]=[C:2]([N:26]2[C:27]3[C:23](=[CH:22][C:21]([O:28][CH3:29])=[CH:20][C:19]=3[Cl:18])[CH2:24][CH2:25]2)[C:3](=[O:16])[N:4]([CH:9]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 184527943,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinoneHCID 184528197-Chloro-5-methoxyindoline hydrochloride

Product 1

HCID 101796055-Chloro-3-(7-chloro-5-methoxy-2,3-dihydro-1H-indol-1-yl)-1-(1-cyclobutylpropyl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinone and 7-chloro-5-methoxyindoline hydrochloride as the starting materials to give a yellow oil. 1H NMR (300 MHz, CDCl3): δ 6.74 (s, 2H), 6.67 (s, 1H), 4.90–4.80 (m, 1H), 4.34 (t, J=7.9 Hz, 2H), 3.78 (s, 3H), 3.10 (t, J=7.7 Hz, 2H), 2.60–2.50 (m, 1H), 2.18–2.12 (m, 1H), 1.90–1.70 (m, 6H), 1.55–1.43 (m, 1H), 0.84 (t, J=7.5 Hz, 3H); HRMS (ESI) m/z 408.1270 [(M+H)+, calcd for C20H24N3O2Cl2 408.1246].

Workup

  1. customPrepared in a similar fashion
  2. customto give a yellow oil

Sources & evidence

ORD record
ord-2647714e7f3e441f9f44d3e6e682504b
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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