Acetic Anhydride → HCID 57974295, compound

HRID 1864338Notes

Reaction equation

[CH3:1][C@H:2]([O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=3)=[C:20]([CH3:32])[CH:19]=1)=[N:10][CH:11]=[N:12]2)[CH2:3][NH:4][CH3:5].[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[CH3:5][N:4]([CH2:3][C@@H:2]([O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=3)=[C:20]([CH3:32])[CH:19]=1)=[N:10][CH:11]=[N:12]2)[CH3:1])[C:33](=[O:35])[CH3:34]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 69059442HCID 69059442, compound

Product 1

HCID 57974295HCID 57974295, compoundYield 64%

Procedure

The procedure described in Example 104 was repeated using 5-[(1S)-1-methyl-2-(methylamino)ethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine (obtained as described in Example 109, preparation of starting materials) and acetic anhydride to give the title compound in 64% yield; NMR spectrum (CDCl3) 1.55 (d, 3H), 2.08 (s, 3H), 2.30 (s, 3H), 2.53 (s, 3H), 3.08 (s, 3H), 3.56 (dd, 1H), 3.93 (dd, 1H), 5.09 (m, 1H), 6.92 (d, 1H), 7.12 (m, 3H), 7.50 (m, 2H), 7.65 (m, 1H), 7.70 (s, 1H), 8.27 (s, 1H), 8.62 (s, 1H); Mass spectrum: MH+ 472.

Sources & evidence

ORD record: ord-34741716cbef4e74a1e9c0129b4586c1
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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