Water → HCID 53918232, compound

HRID 394745Notes

Reaction equation

HRID 394745 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH2:13][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]([Br:31])[CH:26]=1.[F:32][C:33]([F:40])([F:39])[CH:34]=[CH:35][C:36](O)=[O:37].O>C1COCC1.CN(C=O)C>[Br:31][C:27]1[CH:26]=[C:25]([NH:24][C:17]2[C:16]3[C:21](=[CH:22][CH:23]=[C:14]([NH:13][C:36](=[O:37])[CH:35]=[CH:34][C:33]([F:40])([F:39])[F:32])[CH:15]=3)[N:20]=[CH:19][N:18]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27824314,4,4-Trifluoro-but-2-enoic acidHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 53918232HCID 53918232, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (192 mg, 1.0 mmol) was added to a solution of 6-amino-4[(3-bromophenyl)amino]quinazoline (158 mg, 0.5 mmol) and 4,4,4,-trifluorobut-2-enoic acid (153 mg, 1.1 mmol) in THF/DMF (4:1, 2.5 mL), stirred under nitrogen at 0° C. After 1 hour water (10 mL) was added and after 15 minutes the precipitate was collected by Buchner filtration. The residue was rinsed with water (2×5 mL) and ether (10 mL) and air dried. The solid was suspended in EtOAc, (10 mL) refluxed briefly, and sonicated for 10 minutes, and the solid was collected by Buchner filtration, rinsed with EtOAc (5 mL) and dried in a vacuum oven at 75° C. for 1.5 hours to give N-[4-[(3-bromophenyl)amino]-quinazolin-6-yl]4,4,4-trifluorobut-2-enamide 0.4 hydrochloride (76 mg, 33%) as a light yellow solid, mp 273-278° C.

Workup

  1. filtrationwas collected by Buchner filtration
  2. washThe residue was rinsed with water (2×5 mL) and ether (10 mL) and air
  3. customdried
  4. temperaturerefluxed briefly
  5. customsonicated for 10 minutes
  6. filtrationthe solid was collected by Buchner filtration
  7. washrinsed with EtOAc (5 mL)
  8. customdried in a vacuum oven at 75° C. for 1.5 hours

Sources & evidence

ORD record
ord-89dd1cd90e7b4b4f8bced6bfa7e92fac
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

Loading…