Acetyl chloride → HCID 11386635, compound

HRID 1864221Notes

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][OH: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][OH: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 69055369HCID 69055369, compound

Product 1

HCID 11386635HCID 11386635, compoundYield 21%

Procedure

The procedure described in Example 5 was repeated using 2-({2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}amino)ethanol and acetyl chloride to give the title compound in 21% yield; NMR spectrum (DMSO-d6) 2.00 (s, 3H), 3.43 (t, 2H), 3.54-3.59 (m, 2H), 3.88-3.97 (m, 2H), 4.41 (t, 2H), 4.85 (t, 1H), 5.31 (s, 2H), 7.16 (d, 1H), 7.25 (d, 1H), 7.33 (d, 1H), 7.35-7.40 (m, 1H), 7.57-7.62 (m, 2H), 7.70-7.75 (m, 1H), 7.86-7.92 (m, 1H), 7.96 (d, 1H), 8.45 (s, 1H), 8.61 (d, 1H), 9.83 (s, 1H); Mass spectrum MH+ 508.

Sources & evidence

ORD record: ord-831034da347b4028b41c48f56dbe78b5
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

Loading…