Acrylic Acid → HCID 10520057, compound

HRID 394729Notes

Reaction equation

Cl.C[N:3](C)[CH2:4][CH2:5][CH2:6]N=C=NCC.N[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][N:18]=[C:17]2[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1.C(O)(=[O:35])C=C>CN(C)C=O>[Cl:31][C:27]1[CH:26]=[C:25]([NH:24][C:17]2[C:16]3[C:21](=[CH:22][C:23]([NH:3][C:4](=[O:35])[CH:5]=[CH2:6])=[CH:14][CH:15]=3)[N:20]=[CH:19][N:18]=2)[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol) was added to a solution of 6-amino-4[(3-chlorophenyl)amino]quinazoline (136 mg, 0.5 mmol) and acrylic acid (108 mg, 1.5 mmol) in dimethylformamide (DMF) (5 mL), stirred under nitrogen at 0° C. After 15 minutes the reaction mixture was stirred at 25° C. for 18 hours, and then poured onto ice-water (50 mL) and after 1 hour the precipitate was collected by Buchner filtration. The residue was rinsed, air dried, dissolved in the minimum of 25° C. methanol (MeOH) (60 mL), concentrated at 25° C. under reduced pressure to below 10 mL, and recrystallized at 0° C. to give N-[4-[(3-chlorophenyl)-amino]quinazolin-7-yl]acrylamide (33 mg, 20%) as a light orange solid, mp 296.5-298.5° C.

Workup

stirringAfter 15 minutes the reaction mixture was stirred at 25° C. for 18 hours
additionpoured onto ice-water (50 mL) and after 1 hour the precipitate
filtrationwas collected by Buchner filtration
washThe residue was rinsed
customair dried
dissolutiondissolved in the minimum of 25° C. methanol (MeOH) (60 mL)
concentrationconcentrated at 25° C. under reduced pressure to below 10 mL
customrecrystallized at 0° C.

Sources & evidence

ORD record: ord-0319b1dc4bd54effbe8449a2934248b7
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06602863B1

Reaction notes

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