Hydrochloric Acid → 7-(2,5-Dibromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

HRID 1700669노트

반응식

HRID 1700669 반응식
[Br:1][C:2]1[S:3][C:4]([Br:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=O)[CH2:8]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:31][NH:32][C:33]([NH:35][OH:36])=[NH:34].[ClH:37]>C(O)C>[ClH:37].[Br:1][C:2]1[S:3][C:4]([Br:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[N:31][NH:32][C:33](=[NH:34])[NH:35][OH:36])[CH2:8]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 183174087-(2,5-Dibromothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178427660HCID 178427660, 화합물

생성물 1

HCID 1784281547-(2,5-Dibromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a mixture of 7-(2,5-dibromothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.07 g) and 1-amino-3-hydroxyguanidine p-toluenesulfonate (58 mg) were added ethanol (1.5 ml) and concentrated hydrochloric acid (0.04 ml), and the mixture was stirred at 90° C. for 2 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added 0.2N sodium hydroxide solution (10 ml). The mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (20 ml). The organic layer was washed with water, to which was added concentrated hydrochloric acid (0.02 ml). The mixture was concentrated, and to the residue was added ethanol (1 ml). To the solution was added ether (0.2 ml), and the mixture was stirred for 3 hours. Precipitated crystals were filtered, washed with a mixture of ethanol/ether and dried to give 7-(2,5-dibromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 126) (0.27 g) as pale yellow crystals.

후처리

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue was added 0.2N sodium hydroxide solution (10 ml)
  3. extractionThe mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (20 ml)
  4. washThe organic layer was washed with water, to which
  5. additionwas added concentrated hydrochloric acid (0.02 ml)
  6. concentrationThe mixture was concentrated
  7. additionto the residue was added ethanol (1 ml)
  8. additionTo the solution was added ether (0.2 ml)
  9. stirringthe mixture was stirred for 3 hours
  10. customPrecipitated crystals
  11. filtrationwere filtered
  12. washwashed with a mixture of ethanol/ether
  13. customdried

출처 및 근거

ORD 기록
ord-5531f1942e174c7ea840f8852df2c5dd
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350749B1

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