Acetyl chloride → HCID 57974353, compound

HRID 1864214Notes

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][CH:32]3[CH2:34][CH2:33]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]([CH2:31][CH:32]3[CH2:34][CH2:33]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 69057826HCID 69057826, compound

Product 1

HCID 57974353HCID 57974353, compoundYield 58%

Procedure

The procedure described in Example 5 was repeated using N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-{2-[(cyclopropylmethyl)amino]ethoxy}quinazolin-4-amine and acetyl chloride to give the title compound in 58% yield; NMR spectrum (DMSO-d6) 0.16-0.27 (m, 2H), 0.36-0.52 (m, 2H), 0.97-1.06 (m, 1H), 2.00 (s, 3H), 3.24-3.29 (m, 2H), 3.93-4.02 (m, 2H), 4.33-4.56 (m, 2H), 5.31 (s, 2H), 7.13-7.18 (m, 1H), 7.21-7.29 (m, 1H), 7.31-7.40 (m, 2H), 7.54-7.62 (m, 2H), 7.69-7.79 (m, 1H), 7.86-7.92 (m, 1H), 7.93-7.96 (m, 1H), 8.44 (s, 1H), 8.61 (d, 1H), 9.81 (s, 1H); Mass spectrum MH+ 518.

Sources & evidence

ORD record: ord-d0de9f06b96d46079e4aa3ff5121a29e
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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