3-Butynoic Acid → HCID 5329076, compound

HRID 394764Notes

Reaction equation

HRID 394764 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1.[C:20](O)(=[O:24])[CH2:21][C:22]#[CH:23].Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:20](=[O:24])[CH:21]=[C:22]=[CH2:23])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1375473-Butynoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 5329076HCID 5329076, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-amino-4-[(3-bromophenyl)amino]quinazoline (316 mg, 1.0 mmol), and 3-butynoic acid (173 mg, 2.06 mmol) in DMF (5 mL) stirred under nitrogen at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (384 mg, 2.0 mmol). After 1.5 hours the reaction was quenched with 0.1 M HCl solution (10 mL). The yellow precipitate was collected by Buchner filtration and washed with water followed by acetone. The solid was taken up into acetone with the addition of triethylamine. The formed solution was filtered through a 2-inch silica gel eluting with 50% acetone/CH2Cl2. The filtrate was collected and concentrated under reduced pressure to give the title compound as a yellow solid (247 mg, 56%), mp 268-270° C.

Workup

  1. customAfter 1.5 hours the reaction was quenched with 0.1 M HCl solution (10 mL)
  2. filtrationThe yellow precipitate was collected by Buchner filtration
  3. washwashed with water
  4. additionThe solid was taken up into acetone with the addition of triethylamine
  5. filtrationThe formed solution was filtered through a 2-inch silica gel eluting with 50% acetone/CH2Cl2
  6. customThe filtrate was collected
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d377bad15c7c435d8af1707e917abec5
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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