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Calcium Carbonate → 2,2-Dimethylpropanoic acid, [6-[[(4-acetylphenyl)-2-propynylamino]methyl]-4-oxo-3(4H)-quinazolinyl]methyl ester

HRID 1722695
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HRID 1722695 반응식
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([O:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18]Br)[CH:14]=2)[N:9]=[CH:8]1)=[O:4].[CH2:22]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=1)[C:23]#[CH:24].C(=O)([O-])[O-].[Ca+2]>CC(N(C)C)=O>[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([O:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][N:25]([C:26]3[CH:27]=[CH:28][C:29]([C:32](=[O:34])[CH3:33])=[CH:30][CH:31]=3)[CH2:22][C:23]#[CH:24])[CH:14]=2)[N:9]=[CH:8]1)=[O:4]
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참가 물질

5

반응물 3

HCID 10112Calcium CarbonateHCID 11469351Ethanone, 1-[4-(2-propynylamino)phenyl]-HCID 136912136-Bromomethyl-3,4-dihydro-4-oxo-3-((pivaloyl)oxy)methylquinazoline

생성물 1

HCID 146499992,2-Dimethylpropanoic acid, [6-[[(4-acetylphenyl)-2-propynylamino]methyl]-4-oxo-3(4H)-quinazolinyl]methyl ester수율 186.8%

시약·촉매·용매 1

HCID 31374
Dimethylacetamide
용매

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온도
80 °C

실험 절차

A suspension of 5.79 g (12.5 mmol) of 75% pure 2,2-dimethylpropanoic acid, [6-(bromomethyl)-4-oxo-3(4H)-quinazolinyl]methyl ester (European patent application 204,529), 2.89 g (16.7 mmol) of 1-[4-(2-propynylamino)phenyl]ethanone (see Example A), and 3.34 g (33.4 mmol) of dry calcium carbonate in 100 ml of dimethylacetamide (DMA) is stirred at 80° C. for eighteen hours. The suspension is poured into a water-ice mixture and stirred. The suspension is extracted with ethyl acetate. The ethyl acetate solution is dried (magnesium sulfate) and concentrated to give 10.4 g of a yellow oil. This is dissolved in a minimum amount of dichloromethane and applied to a column of 1 kg of flash silica gel packed in dichloromethane/methanol (100:1). Elution with the same solvent gives 2.83 g (50.8%) of impure product as a yellow gum followed by 2.34 g (42.0% assuming 75% pure bromomethyl compound) of the product as a cream colored foam. This is used as is without characterization in the next reaction.

후처리

  1. stirringstirred
  2. extractionThe suspension is extracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution is dried (magnesium sulfate)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-396b2db1f812405dbccb6f68348679a1
출처 데이터셋
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04857530

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