1-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone → HCID 10274881, compound

HRID 1271156Notes

Reaction equation

HRID 1271156 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.[Br:17][C:18]1[CH:19]=[C:20]([O:27][CH3:28])[CH:21]=[C:22]2[C:26]=1[NH:25][CH2:24][CH2:23]2>>[Br:17][C:18]1[CH:19]=[C:20]([O:27][CH3:28])[CH:21]=[C:22]2[C:26]=1[N:25]([C:2]1[C:3](=[O:15])[N:4]([C@H:9]([CH:12]3[CH2:14][CH2:13]3)[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1)[CH2:24][CH2:23]2

Participants

3

Reactant 2

HCID 184528011-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinoneHCID 184528177-Bromo-5-methoxyindoline hydrochloride

Product 1

HCID 10274881HCID 10274881, compound

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[(1S)-1-cyclopropylpropyl]-2(1H)-pyrazinone and 7-bromo-5-methoxyindoline hydrochloride as the starting materials. mp 138–140° C.; 1H NMR (300 MHz, CDCl3): δ 6.94 (s, 1 H), 6.89 (d, J=2.2 Hz, 1 H), 6.76 (d, J=2.2 Hz, 1 H), 4.34–4.24 (m, 2 H), 4.10–4.01 (m, 1 H), 3.76 (s, 3 H), 3.09 (t, J=7.9 Hz, 2 H), 1.94–1.74 (m, 2 H), 1.06–0.98 (m, 1 H), 0.95–0.86 (m, 3 H), 0.79–0.72 (m, 1 H), 0.54–0.44 (m, 2 H), 0.35–0.22 (m, 1 H); HRMS (ESI) calcd for C19H22N3O2BrCl (M+H)+: 438.0584; found m/z 438.0605.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-3ce1808a522f4c3ab2aa072747b614c7
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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