Triethylamine → N-{4-[(3-Chloro-4-thiophenoxyphenyl)amino]-3-cyano-6-quinolinyl}-2-propenamide

HRID 612236Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:17]([Cl:28])[CH:16]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:39])[CH:37]=[CH2:38].C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1>[Cl:28][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:36](=[O:39])[CH:37]=[CH2:38])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][C:18]=1[S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolved 1.00 g (2.48 mmol) 6-amino-4-[(3-chloro-4-thiophenoxyphenyl)amino]-3-quinolinecarbonitrile in 2.0 ml DMF and 12 ml THF and chilled to 0° C under N2. Added 380 μl (2.73 mmol) triethylamine and 227 μl (2.73 mmol) acryloyl chloride. Removed ice bath at 15 minutes and at 1.5 hours stripped solvent and slurried residue with dilute sodium bicarbonate. Collected solids and washed with water. Recrystallized from ethyl acetate and dried in vacuo, giving 293 mg of yellow-orange solid: mass spectrum (electrospray m/e): M+H=457.3. 459.3.

Workup

waitat 1.5 hours stripped
customCollected solids
washwashed with water
customRecrystallized from ethyl acetate
customdried in vacuo

Sources & evidence

ORD record: ord-ed914c07df80422ea6b747060262e4a5
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

Loading…