Water → HCID 178486716, compound

HRID 749158Notes

Reaction equation

HRID 749158 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]([OH:30])=[O:29])[CH:23]=1.O>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]([OH:30])=[O:29])[CH:23]=3)=[N:14][CH:13]=[N:12]2)=[CH:8][C:7]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 11551084HCID 11551084, compoundHCID 178507647HCID 178507647, compound

Product 1

HCID 178486716HCID 178486716, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Alternatively, N′-(5-(3-chloropropoxy)-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide (14.78 g, 50 mmol) in acetic acid (40 ml) was heated at reflux with (5-amino-1H-pyrazol-3-yl) acetic acid (8.1 g, 57.5 mmol) for 1.5 h. The reaction mixture was cooled to ambient temperature, water (250 ml) was added to the mixture and the solid was recovered by suction filtration. The solid was washed with 1) water, ii) ethyl acetate and iii) diethyl ether and dried in vacuo at 50° C. to yield (5-((7-(3-chloropropoxy)-6-methoxy-quinazolin-4-yl)amino)-1H-pyrazol-3-yl)acetic acid as a yellow solid (13.6 g, 69% yield):

Workup

  1. filtrationthe solid was recovered by suction filtration
  2. washThe solid was washed with 1) water, ii) ethyl acetate and iii) diethyl ether
  3. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-93e3666470904df3bf3ae144ab151256
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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