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

HRID 2251018Notes

Reaction equation

HRID 2251018 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.[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[C:24]([Br: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]([Br:16])=[CH:25][C:24]=3[Br: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 184527991-[(1R)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinoneHCID 18629224HCID 18629224, compound

Product 1

HCID 101410555-Chloro-1-[(1R)-1-cyclopropylpropyl]-3-(5,7-dibromo-2,3-dihydro-1H-indol-1-yl)-2(1H)-pyrazinone

Procedure

Part B: Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[(1R)-1-cyclopropylpropyl]-2(1H)-pyrazinone and 5,7-dibromoindoline as the starting materials. mp 164-165° C.; 1H NMR (300 MHz, CDCl3): δ 7.42 (d, J=1.8 Hz, 1 H), 7.22 (d, J=1.5 Hz, 1 H), 6.96 (s, 1 H), 4.26 (t, J=8.1 Hz, 2 H), 3.99 (app. q, J=8.3 Hz, 1 H), 3.08 (t, J=7.9 Hz, 2 H), 1.94-1.69 (m, 2 H), 1.02-0.92 (m, 1 H), 0.87 (t, J=7.5 Hz, 3 H), 0.78-0.68 (m, 1 H), 0.50-0.39 (m, 2 H), 0.29-0.22 (m, 1 H); HRMS (ESI) calcd for C18H19N3OBr2Cl (M+H)+: 485.9583; found m/z 485.9592.

Workup

  1. customPart B: Prepared in a similar fashion

Sources & evidence

ORD record
ord-45cb59fca81a4ffe9dfe33199d074a2a
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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