Acetyl chloride → HCID 11443769, compound

HRID 1864216Notes

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][CH:31]3[CH2:34][CH2:33][CH2:32]3)[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:35](Cl)(=[O:37])[CH3:36]>>[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]([CH:31]3[CH2:34][CH2:33][CH2:32]3)[C:35](=[O:37])[CH3:36])[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 69056159HCID 69056159, compound

Product 1

HCID 11443769HCID 11443769, compoundYield 42%

Procedure

The procedure described in Example 5 was repeated using N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(cyclobutylamino)ethoxy]quinazolin-4-amine and acetyl chloride to give the title compound in 42% yield; NMR spectrum (DMSO-d6) 1.50-1.65 (m, 2H), 2.01 s, 3H), 2.12-2.21 (m, 4H), 3.94 (t, 2H), 4.28-4.38 (m, 3H), 5.31 (s, 2H), 7.19 (d, 1H), 7.26 (d, 1H), 7.32-7.40 (m, 2H), 7.57-7.62 (m, 2H), 7.69-7.76 (m, 1H), 7.86-7.91 (m, 1H), 7.97 (s, 1H), 8.45 (s, 1H), 8.60 (d, 1H), 9.90 (s, 1H); Mass spectrum MH+ 518.

Sources & evidence

ORD record: ord-81557cd11e6a41d280784d77d51dd096
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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