Triethylamine → 4-(6-Acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole

HRID 1491856노트

반응식

HRID 1491856 반응식
[C:1]([O:4][CH2:5][C:6](Cl)=[O:7])(=[O:3])[CH3:2].Cl.Cl.Cl.[NH2:12][CH2:13][C:14]1[N:19]=[C:18]([C:20]2[N:21]=[C:22]([N:25]=[C:26]([NH2:28])[NH2:27])[S:23][CH:24]=2)[CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.C(=O)([O-])[O-:37].[K+].[K+].[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43]>ClCCl.O.O1CCCC1>[C:1]([O:4][CH2:5][C:6]([NH:12][CH2:13][C:14]1[N:19]=[C:18]([C:20]2[N:21]=[C:22]([N:25]=[C:26]([NH:28][C:47](=[O:37])[CH2:46][O:45][C:42](=[O:44])[CH3:43])[NH2:27])[S:23][CH:24]=2)[CH:17]=[CH:16][CH:15]=1)=[O:7])(=[O:3])[CH3:2]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 26297Acetoxyacetyl chlorideHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

생성물 1

HCID 538938594-(6-Acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Acetoxyacetyl chloride (0.7 g) was added to a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g) and triethylamine (2.6 ml) in dichloromethane (30 ml) under ice-cooling and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was added to a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was separated and purified by column chromatograpy on silica gel, and eluted with a mixture of chloroform and methanol (9:1, V/V). The eluted fast fractions containing the desired were collected and evaporated in vacuo to give 4-(6-acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole (0.3 g).

후처리

  1. temperaturecooling
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was separated
  6. custompurified by column chromatograpy on silica gel
  7. washeluted with a mixture of chloroform and methanol (9:1, V/V)
  8. washThe eluted fast fractions
  9. additioncontaining the
  10. customdesired were collected
  11. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-484ed975921a4cefaf71e1b13259d946
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371097

반응 노트

불러오는 중…