Potassium Carbonate → But-2-ynoic acid [4-(3-dimethylamino-phenylamino)-quinazolin-6-yl]-amide

HRID 1069008Notes

Reaction equation

HRID 1069008 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:19])[C:16]#[C:17][CH3:18])[CH:6]=[CH:7][C:8]=1[N:9]=[CH:10][N:11](C)C)#[N:2].Cl.Cl.[CH3:22][N:23]([CH3:31])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26](N)[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(#N)C>[CH3:22][N:23]([CH3:31])[C:24]1[CH:25]=[C:26]([NH:2][C:1]2[C:3]3[C:8](=[CH:7][CH:6]=[C:5]([NH:14][C:15](=[O:19])[C:16]#[C:17][CH3:18])[CH:4]=3)[N:9]=[CH:10][N:11]=2)[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 18350692N-[3-Cyano-4-[[(dimethylamino)methylene]amino]phenyl]-2-butynamide

Product 1

HCID 9946151But-2-ynoic acid [4-(3-dimethylamino-phenylamino)-quinazolin-6-yl]-amideYield 58.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.54 grams (0.01 moles) of but-2-ynoic acid [3-cyano-4-(dimethylamino-methyleneamino)-phenyl]-amide, 2.40 grams (0.0115 moles) of N, N-dimethyl-1,3-phenylenediamine dihydrochloride, and 1.59 grams (0.0115 moles) of potassium carbonate in 2.5 mL of glacial acetic acid and 5 mL of acetonitrile was refluxed for an hour. On cooling the solid was filtered and recrystallized from methyl cellusolve to give 2.02 grams (58%) of the desired product, which melted at 252-254° C. MS M+H=346.1.

Workup

  1. temperaturewas refluxed for an hour
  2. temperatureOn cooling the solid
  3. filtrationwas filtered
  4. customrecrystallized from methyl cellusolve

Sources & evidence

ORD record
ord-eb7e7e5b64bb4414b505ee7809d43b83
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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