Hydrochloric Acid → HCID 18176191, compound

HRID 394735Notes

Reaction equation

HRID 394735 reaction equation
[ClH:1].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]([C:31]([F:34])([F:33])[F:32])[CH:26]=1.N1C=CC=CC=1.Cl.[CH2:42]1C[O:45][CH2:44][CH2:43]1.CN(C=O)C>>[ClH:1].[F:32][C:31]([F:33])([F:34])[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:44](=[O:45])[CH:43]=[CH2:42])[CH:15]=3)[N:20]=[CH:19][N:18]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53281884-N-[3-(trifluoromethyl)phenyl]quinazoline-4,6-diamineHCID 21974620tetrahydrofuran N,N-dimethylformamide

Product 1

HCID 18176191HCID 18176191, compoundYield 45%

Conditions

Temperature
0 °C

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (212 mg, 1.1 mmol) was added to a solution of 6-amino-4[(3-(trifluoromethyl)phenyl)-amino]quinazoline (153 mg, 0.5 mmol) acrylic acid (73 mg, 1.0 mmol) and pyridine (206 mg, 2.5 mmol) in THF/DMF (4:1, 2.5 mL), stirred under nitrogen at 0° C. After 15 minutes the reaction mixture was stirred at 25° C. for 1 hour, and then recooled to 0° C. Dilute hydrochloric acid (0.5 M, 10 mL) was added, and after 15 minutes the precipitate was collected by Buchner filtration. The residue was rinsed with water (5 mL) and ether (2×5 mL) and dried in a vacuum oven at 75° C. overnight to give N-[4-[(3-(trifluoromethyl)phenyl)amino]quinazolin-6-yl]acrylamide hydrochloride (87 mg, 45%) as a light greenish solid, mp 195-199° C.

Workup

  1. stirringAfter 15 minutes the reaction mixture was stirred at 25° C. for 1 hour
  2. customrecooled to 0° C
  3. filtrationafter 15 minutes the precipitate was collected by Buchner filtration
  4. washThe residue was rinsed with water (5 mL) and ether (2×5 mL)
  5. customdried in a vacuum oven at 75° C. overnight

Sources & evidence

ORD record
ord-6bb2bc10c3b848af8da375c881240b09
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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