Diethyl Ether → HCID 178493320, compound

HRID 749191Notes

Reaction equation

HRID 749191 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[N:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:27]=[C:26]([CH2:28][C:29]([OH:31])=[O:30])[NH:25][N:24]=1.C(OCC)C>CC(N(C)C)=O.Cl.O1CCOCC1>[CH3:21][O:20][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:22][C:23]3[NH:24][N:25]=[C:26]([CH2:28][C:29]([OH:31])=[O:30])[CH:27]=3)=[N:3][CH:4]=[N:5]2)=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:9]=1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 113812714-Chloro-7-methoxy-5-[(1-methylpiperidin-4-yl)oxy]quinazolineHCID 16221512(5-Amino-2H-pyrazol-3-yl)-acetic acid

Product 1

HCID 178493320HCID 178493320, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Procedure

4-chloro-7-methoxy-5-[(1-methylpiperidin-4-yl)oxy]quinazoline (307 mg, 0.85 mmol) was condensed with (3-amino-1H-pyrazol-5-yl)acetic acid (132 mg, 0.93 mmol) in dimethylacetamide (3 ml) and hydrochloric acid in dioxane (4.0 N solution, 467 μl) at 90° C. for 1 hour. The solvent was evaporated, and the residual oil was triturated with ethanol:diethyl ether to yield [5-({7-methoxy-5-[(1-methylpiperidin-4-yl)oxy]quinazolin-4-yl}amino)-1H-pyrazol-3-yl]acetic acid as a beige solid (320 mg, 78% yield):

Workup

  1. customThe solvent was evaporated
  2. customthe residual oil was triturated with ethanol

Sources & evidence

ORD record
ord-bd393d33badc446dad2f0f8b2ddd994b
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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