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

HRID 1271151Notes

Reaction equation

HRID 1271151 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4]([C@@H:9]([CH:12]2[CH2:14][CH2:13]2)[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]([CH:12]2[CH2:14][CH2:13]2)[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 124822955,7-DichloroindolineHCID 184527991-[(1R)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone

Product 1

HCID 101355255-Chloro-1-[(1R)-1-cyclopropylpropyl]-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[(1R)-1-cyclopropylpropyl]-2(1H)-pyrazinone and 5,7-dichloroindoline as the starting materials. mp 166–168° C.; 1H NMR (300 MHz, CDCl3): δ 7.15 (s, 1 H), 7.09 (s, 1 H), 6.99 (s, 1 H), 4.34–4.24 (m, 2 H), 4.08–3.99 (m, 1 H), 3.11 (t, J=8.1 Hz, 2 H), 2.12–2.05 (m, 1 H), 1.92–1.76 (m, 1 H), 1.05–1.00 (m, 1 H), 0.94–0.86 (m, 3 H), 0.80–0.71 (m, 1 H), 0.53–0.46 (m, 2 H), 0.33–0.21 (m, 1 H); HRMS (ESI) calcd for C18H19N3OCl3 (M+H)+: 398.0594; found m/z 398.0575.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-505633e8ed2c4482bef11b6629628715
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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