HCID 11551084, compound → HCID 178499499, compound

HRID 1473840Notes

Reaction equation

HRID 1473840 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.N[C:22]1[NH:26][N:25]=[C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:23]=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:22]3[NH:26][N:25]=[C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:23]=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 reacted with methyl (5-amino-1H-pyrazol-3-yl)acetate (CAS 174891-10-2; WO 95/33724) (110 mg, 0.74 mmol) at reflux for 1 hour. The mixture was cooled, the acetic acid evaporated, and the residue purified by chromatography on silica gel, eluting with dichloromethane/1% methanolic ammonia (90:10), to give 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 evaporated
  4. customthe residue purified by chromatography on silica gel
  5. washeluting with dichloromethane/1% methanolic ammonia (90:10)

Sources & evidence

ORD record
ord-e5a823da54014b6899ef5d8cbce591c9
Source dataset
uspto-grants-2015_04
Patent number
US09018191B2

Reaction notes

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