1-[(1R)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone → 5-Chloro-3-(7-chloro-6-fluoro-5-methoxy-2,3-dihydro-1H-indol-1-yl)-1-[(1R)-1-cyclopropylpropyl]-2(1H)-pyrazinone

HRID 2251019Notes

Reaction equation

HRID 2251019 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[C:18]([F:28])=[C:19]([O:26][CH3:27])[CH:20]=[C:21]2[C:25]=1[NH:24][CH2:23][CH2:22]2>>[Cl:8][C:6]1[N:7]=[C:2]([N:24]2[C:25]3[C:21](=[CH:20][C:19]([O:26][CH3:27])=[C:18]([F:28])[C:17]=3[Cl:16])[CH2:22][CH2:23]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 184528207-Chloro-6-fluoro-5-methoxyindoline

Product 1

HCID 102017175-Chloro-3-(7-chloro-6-fluoro-5-methoxy-2,3-dihydro-1H-indol-1-yl)-1-[(1R)-1-cyclopropylpropyl]-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 7-chloro-6-fluoro-5-methoxyindoline as the starting materials. mp 128-130° C.; 1H NMR (300 MHz, CDCl3): δ 6.96 (s, 1 H), 6.79 (d, J=7.3 Hz, 1 H), 4.33 (t, J=7.9 Hz, 2H), 4.08-4.00 (m, 1 H), 3.86 (s, 3 H), 3.08 (t, J=7.7 Hz, 2 H), 1.94-1.74 (m, 2 H), 1.07-0.97 (m, 1 H), 0.92 (t, J=7.3 Hz, 3 H), 0.80-0.73 (m, 1 H), 0.55-0.44 (m, 2 H), 0.34-0.27 (m, 1H); HRMS (ESI) calcd for C19H21N3O2Cl2F (M+H)+: 412.0995; found m/z 412.1019.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-11469d33d05f45848a2c51645199722c
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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