Propiolic Acid → HCID 9907221, compound

HRID 394746Notes

Reaction equation

HRID 394746 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.[C:32](O)(=[O:35])[C:33]#[CH:34]>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:32](=[O:35])[C:33]#[CH:34])[CH:15]=3)[N:20]=[CH:19][N:18]=2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10110Propiolic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 9907221HCID 9907221, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (200 mg, 1.04 mmol) was added to a solution of 6-amino-4-[(3-bromophenyl)-amino]quinazoline (158 mg, 0.5 mmol) and propiolic acid (0.08 mL, 1.1 mmol) in DMF (1.5 mL) stirred under N2 at 0° C. The resulting solution was stirred at 0° C. for 30 minutes and quenched with water. The formed fine solid was collected by Buchner filtration then dissolved in methanol and purified by preparative tlc on silica, eluting with 10% MeOH/CHCl3. The title compound was isolated as a yellow solid (21 mg, 12%), mp>310° C.

Workup

  1. stirringThe resulting solution was stirred at 0° C. for 30 minutes
  2. customquenched with water
  3. filtrationThe formed fine solid was collected by Buchner filtration
  4. dissolutionthen dissolved in methanol
  5. custompurified by preparative tlc on silica
  6. washeluting with 10% MeOH/CHCl3

Sources & evidence

ORD record
ord-33420285586c4275896ed05d57b66bbc
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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