beta-Alanine, ethyl ester, hydrochloride → 10-(2-Ethoxycarbonylethylamino)-7-chloro-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione

HRID 3139

반응식

HRID 3139 반응식
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([NH:19]N)=[C:8]3[C:16](=[O:17])[NH:15][NH:14][C:13](=[O:18])[C:9]3=[N:10][C:11]=2[CH:12]=1.Cl.[CH2:22]([O:24][C:25](=[O:29])[CH2:26][CH2:27]N)[CH3:23]>N1C=CC=CC=1.O>[CH2:22]([O:24][C:25]([CH2:26][CH2:27][NH:19][C:7]1[C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:12][C:11]=2[N:10]=[C:9]2[C:13](=[O:18])[NH:14][NH:15][C:16](=[O:17])[C:8]=12)=[O:29])[CH3:23]

참가 물질

5

반응물 2

HCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 189299057-Chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride

생성물 1

HCID 1892994110-(2-Ethoxycarbonylethylamino)-7-chloro-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione수율 13%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

A mixture of 7-chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride (1.0 g, 2.9 mM, as prepared in Example 44) and beta alanine ethyl ester hydrochloride (49.0 g, 320 mM) in pyridine (52 mL) was refluxed for 23 hr. After cooling, the vigorously stirred reaction mixture was diluted slowly with water (100mL) and then filtered to separate a fine red solid. The collected solids were washed with water and chromatographed (eluant: methanol/methylene chloride; 5/95) over silica gel to provide the title ester (0.13 g, 13%) as a red powder, mp 258°-260° C.; MS(CI): 363 (M+H).

후처리

  1. temperaturewas refluxed for 23 hr
  2. temperatureAfter cooling
  3. customthe vigorously stirred reaction mixture
  4. filtrationfiltered
  5. customto separate a fine red solid
  6. washThe collected solids were washed with water
  7. customchromatographed (eluant: methanol/methylene chloride; 5/95) over silica gel

출처 및 근거

ORD 기록
ord-3dd4f599f9304ea3aa6b0fcf1031451d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733910

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