Acetyl chloride → HCID 57974339, compound

HRID 1864210Notes

Reaction equation

[CH2:1]([NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[C:21]([Cl:33])[CH:20]=1)=[N:11][CH:12]=[N:13]2)[CH:2]=[CH2:3].[C:34](Cl)(=[O:36])[CH3:35]>>[CH2:1]([N:4]([CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[C:21]([Cl:33])[CH:20]=1)=[N:11][CH:12]=[N:13]2)[C:34](=[O:36])[CH3:35])[CH:2]=[CH2:3]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 690594755-[2-(allylamino)ethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

Product 1

HCID 57974339HCID 57974339, compoundYield 47%

Procedure

The procedure described in Example 5 was repeated using 5-[2-(allylamino)ethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine and acetyl chloride to give the title compound in 47% yield; NMR spectrum (DMSO-d6) 1.95 (s, 3H), 3.86 (t, 2H), 4.02-4.06 (m, 2H), 4.38 (t, 2H), 5.07-5.18 (m, 2H), 5.31 (s, 2H), 5.82-5.92 (m, 1H), 7.14 (d, 1H), 7.25 (d, 1H), 7.32-7.40 (m, 2H), 7.55-7.61 (m, 2H), 7.70-7.75 (m, 1H), 7.86-7.93 (m, 2H), 8.44 (s, 1H), 8.61 (d, 1H), 9.76 (s, 1H); Mass spectrum MH+ 504.

Sources & evidence

ORD record: ord-ea448461d8694d9fa20e42790606461a
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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