HCID 11551084, compound → HCID 178499499, compound

HRID 749156Notes

Reaction equation

HRID 749156 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:19][CH3:20])=[CH:8][C:9]([C:17]#[N:18])=[C:10]([N:12]=[CH:13][N:14](C)C)[CH:11]=1.[CH3:21][O:22][C:23](=[O:31])[CH2:24][C:25]1[CH:29]=[C:28](N)[NH:27][N:26]=1>C(O)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]2[C:9]([C:17]([NH:18][C:28]3[NH:27][N:26]=[C:25]([CH2:24][C:23]([O:22][CH3:21])=[O:31])[CH:29]=3)=[N:14][CH:13]=[N:12]2)=[CH:8][C:7]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 11551084HCID 11551084, compoundHCID 178499525HCID 178499525, compound

Product 1

HCID 178499499HCID 178499499, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N′-(5-(3-chloropropoxy)-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide (230 mg, 0.78 mmol) in acetic acid (0.7 ml) was heated with methyl(5-amino-1H-pyrazol-3-yl)acetate (110 mg, 0.74 mmol) at reflux for 1 hour. The mixture was cooled, the acetic acid was evaporated in vacuo, and the residue purified by chromatography on silica gel, eluting with methanol:ammonia:dichloromethane (9:1:90), to yield methyl (5-((7-(3-chloropropoxy)-6-methoxyquinazolin-4-yl)amino)-1H-pyrazol-3-yl)acetate (219 mg, 69% yield) as a cream solid:

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe mixture was cooled
  3. customthe acetic acid was evaporated in vacuo
  4. customthe residue purified by chromatography on silica gel
  5. washeluting with methanol:ammonia:dichloromethane (9:1:90)

Sources & evidence

ORD record
ord-3d7cfce495bf491fbb05fb19b56a1725
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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