Water → HCID 53918232, compound

HRID 1698958Notes

Reaction equation

HRID 1698958 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-ce7343106e54412ab3b00c4eebc5def0
Source dataset
uspto-grants-2002_02
Patent number
US06344459B1

Reaction notes

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