Acetyl chloride → HCID 11202933, compound

HRID 1864206Notes

Reaction equation

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

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 69056048HCID 69056048, compound

Product 1

HCID 11202933HCID 11202933, compoundYield 70%

Procedure

The procedure described in Example 5 was repeated using N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(propylamino)ethoxy]quinazolin-4-amine and acetyl chloride to give the title compound in 70% yield; NMR spectrum (DMSO-d6) 0.82 (t, 3H), 1.53-1.59 (m, 2H), 1.97 (s, 3H), 3.27 (s, 2H), 3.86 (t, 2H), 4.39 (t, 2H), 5.31 (s, 2H), 7.17 (d, 1H), 7.25 (d, 1H), 7.33-7.39 (m, 2H), 7.58-7.60 (m, 2H), 7.71-7.75 (m, 1H), 7.87-7.91 (m, 1H), 7.95 (d, 1H), 8.45 (s, 1H), 8.60 (d, 1H), 9.80 (s, 1H); Mass spectrum MH+ 506.

Sources & evidence

ORD record: ord-eb8bab2f1c344becbb9daf675701e72d
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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