3,5-Difluorobenzoyl chloride → HCID 53794285, compound

HRID 2055101Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:27])=[C:6]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N:19]4[CH2:25][CH2:24][CH2:23][N:22]([CH3:26])[CH2:21][CH2:20]4)[CH:15]=3)[N:10]=[CH:9]2)[CH:7]=1.[F:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([F:38])[CH:37]=1)[C:32](Cl)=[O:33]>>[F:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([F:38])[CH:37]=1)[C:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:27])=[C:6]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N:19]4[CH2:25][CH2:24][CH2:23][N:22]([CH3:26])[CH2:21][CH2:20]4)[CH:15]=3)[N:10]=[CH:9]2)[CH:7]=1)=[O:33]

Participants

Reactant 2

HCID 1456003,5-Difluorobenzoyl chloride

HCID 22238161HCID 22238161, compound

Product 1

HCID 53794285HCID 53794285, compound

Procedure

Using an analogous procedure to that described in Example 5, 3-(5-amino-2-methylphenyl)-6-(4-methylhomopiperazin-1-yl)-3,4-dihydroquinazolin-4-one was reacted with 3,5-difluorobenzoyl chloride to give the title compound; NMR Spectrum: (DMSOd6) 1.84-1.96 (m, 2H), 2.05 (s, 3H), 2.25 (s, 3H), 2.42-2.5 (m, 2H), 2.62-2.64 (m, 2H), 3.53 (t, 2H), 3.58-3.64 (m, 2H), 7.24 (d, 1H), 7.38 (m, 1H), 7.40-7.44 (m, 1H), 7.48-7.54 (m, 1H), 7.58 (d, 1H), 7.64-7.67 (m, 2H), 7.75-7.78 (m, 2H), 7.96 (s, 1H), 10.49 (s, 1H); Mass Spectrum: M+H+ 504.

Sources & evidence

ORD record: ord-8cd59ba358af4780b63d61854ce3291e
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332483B2

Reaction notes

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