HCID 11060297, compound → HCID 5328968, compound

HRID 1068973Notes

Reaction equation

HRID 1068973 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][O:24][Si](C(C)(C)C)(C)C)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1>[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 11060297HCID 11060297, compound

Product 1

HCID 5328968HCID 5328968, compoundYield 117.9%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide (300 mg, 0.587 mmol) was dissolved in 60 mL of solution (acetic acid:water:tetrahydrofuran=3:1:1) and stirred at room temperature overnight. The reaction solution was treated with cold brine solution and extracted with ethyl acetate. The ethyl acetate solution was washed with sodium bicarbonate solution and brine. Evaporation of the dry ethyl acetate solution yielded 275 mg of the product: HRMS m/z 397.0258 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with sodium bicarbonate solution and brine
  3. customEvaporation of the dry ethyl acetate solution

Sources & evidence

ORD record
ord-6198449f737e458dbe90a036e56d9979
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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