1-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone → HCID 10112336, compound

HRID 1271160Notes

Reaction equation

HRID 1271160 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 184528011-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinoneHCID 184528207-Chloro-6-fluoro-5-methoxyindoline

Product 1

HCID 10112336HCID 10112336, 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-chloro-6-fluoro-5-methoxyindoline as the starting materials. mp 127–129° 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, 2 H), 4.11–4.00 (m, 1 H), 3.86 (s, 3 H), 3.08 (t, J=7.7 Hz, 2 H), 1.94–1.74 (m, 2 H), 1.07–0.99 (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), 0.34–0.25 (m, 1 H); HRMS (ESI) calcd for C19H21N3O2Cl2F (M+H)+: 412.0995; found m/z 412.1001.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-b10c27679b3a4d0397b181862c8abf39
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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