Pyridine → HCID 67336322, compound

HRID 1675237Notes

Reaction equation

[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)=[C:24]([Cl:37])[CH:23]=1)=[O:4].[C:38](O)(=[O:41])[CH:39]=[CH2:40].N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC>C1COCC1>[Cl:37][C:24]1[CH:23]=[C:22]([NH:21][C:9]2[C:8]3[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:6]([NH:5][C:3]([CH2:2][NH:1][C:38](=[O:41])[CH:39]=[CH2:40])=[O:4])[CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:27]=[CH:26][C:25]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

320 mg of 2-amino-N-{4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-7-(2-methoxyethoxy)-quinazolin-6-yl}-acetamide as a starting material was dissolved in 10 ml of THF, and cooled to 0° C. The solution was reacted with 0.06 ml of acrylic acid, 0.1 ml of pyridine and 234 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at 0° C. for 1 hour and at room temperature for 5 hours. The reacted solution was extracted with a mixture of chloroform and isopropanol after adding saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure, and the resulting residue was subjected to column chromatography (eluent-ethylacetate:methanol=30:1) to obtain the title compound (96 mg, 27%).

Workup

extractionThe reacted solution was extracted with a mixture of chloroform and isopropanol
additionafter adding saturated sodium bicarbonate
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
distillationdistilled under a reduced pressure

Sources & evidence

ORD record: ord-c7f23779e1534612a7d8acbb046936a6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003658B2

Reaction notes

Loading…