1-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone → HCID 10199381, compound

HRID 1271157Notes

Reaction equation

HRID 1271157 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.[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:25](=[C:26]([CH3:28])[CH:27]=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:18][CH3:17])=[CH:27][C:26]=3[CH3:28])[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 184528011-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinoneHCID 18452815HCID 18452815, compound

Product 1

HCID 10199381HCID 10199381, compound

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[(1S)-1-cyclopropylpropyl]-2(1H)-pyrazinone and 5-methoxy-7-methylindoline hydrochloride as the starting materials. mp 156–158° C.; 1H NMR (300 MHz, CDCl3): δ 6.87 (s, 1 H), 6.65 (d, J=1.8 Hz, 1 H), 6.57 (d, J=2.2 Hz, 1 H), 4.35 (t, J=7.7 Hz, 2 H), 4.10–4.02 (m, 1 H), 3.77 (s, 3 H), 3.02 (t, J=7.7 Hz, 2 H), 2.05 (s, 3 H), 1.93–1.73 (m, 2 H), 1.06–0.99 (m, 1 H), 0.95–0.87 (m, 3 H), 0.80–0.73 (m, 1 H), 0.55–0.44 (m, 2 H), 0.34–0.23 (m, 1 H); HRMS (ESI) calcd for C20H25N3O2Cl (M+H)+: 374.1635; found m/z 374.1634.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-1097a704d90c46e2a899b6d43ca6bcf0
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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