Acetic Acid → (3-([7-(4-chlorobutoxy)-6-methoxyquinazolin-4-yl]amino)-1H-pyrazol-5-yl)acetic acid

HRID 749174Notes

Reaction equation

HRID 749174 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([O:20][CH3:21])=[CH:9][C:10]([C:18]#[N:19])=[C:11]([N:13]=[CH:14][N:15](C)C)[CH:12]=1.C(O)(=O)C.N[C:27]1[CH:31]=[C:30]([CH2:32][C:33]([OH:35])=[O:34])[NH:29][N:28]=1>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]2[C:10]([C:18]([NH:19][C:27]3[CH:31]=[C:30]([CH2:32][C:33]([OH:35])=[O:34])[NH:29][N:28]=3)=[N:15][CH:14]=[N:13]2)=[CH:9][C:8]=1[O:20][CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 16221512(5-Amino-2H-pyrazol-3-yl)-acetic acidHCID 68993086N'-[5-(4-chlorobutoxy)-2-cyano-4-methoxyphenyl]-N,N-dimethylimidoformamide

Product 1

HCID 68987817(3-([7-(4-chlorobutoxy)-6-methoxyquinazolin-4-yl]amino)-1H-pyrazol-5-yl)acetic acidYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N′-[5-(4-chlorobutoxy)-2-cyano-4-methoxyphenyl]-N,N-dimethylimidoformamide (464 g, 15 mmol) in acetic acid (13.5 ml, 225 mmol) was reacted with (3-amino-1H-pyrazol-5-yl)acetic acid (2.22 g, 15.8 mmol) at reflux for 1 hour. The mixture was cooled, diluted with ethanol (25 ml) and the resultant precipitate recovered by suction filtration. The solid was stirred in water for 1 hour, collected by suction filtration and dried to yield (3-([7-(4-chlorobutoxy)-6-methoxyquinazolin-4-yl]amino)-1H-pyrazol-5-yl)acetic acid (4.5 g, 74% yield):

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe mixture was cooled
  3. filtrationthe resultant precipitate recovered by suction filtration
  4. filtrationcollected by suction filtration
  5. customdried

Sources & evidence

ORD record
ord-2233b8fd53f14bc9a72fceef8ef92455
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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