Hydrochloric Acid → (S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester

HRID 1609479노트

반응식

HRID 1609479 반응식
Cl.Cl.[CH3:3][C:4]1[CH:5]=[C:6]([CH2:13][N:14]2[C:22]3[CH2:21][C@@H:20]([C:23]([OH:25])=[O:24])[NH:19][CH2:18][C:17]=3[N:16]=[CH:15]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].Cl.[CH3:27]O>COC(OC)OC>[CH3:27][O:24][C:23]([C@H:20]1[NH:19][CH2:18][C:17]2[N:16]=[CH:15][N:14]([CH2:13][C:6]3[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH3:3])[CH:5]=3)[C:22]=2[CH2:21]1)=[O:25]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70345643(S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloride

생성물 1

HCID 14457531(S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester수율 72.3%

시약·촉매·용매 1

HCID 9005Trimethyl orthoformate용매

실험 절차

(S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloride (VII-2) (1.1538g, 0.00296 mol) was suspended in dry methanol (46 ml) and trimethylorthoformate (4.6 ml). Hydrogen chloride was blown into the suspension to saturation under ice cooling and stirring. The reaction solution was then stirred on a 90° C. oil bath for 6 hours, cooled, and concentrated. The resulting yellowish brown oily material (0.7456 g) was purified by silica gel column chromatography (Kiesegel 60, 60 g, chloroform/methanol= 15/1) to obtain the objective compound (VI-2) (0.7076 g; yield: 72.3%) as an orange oily material.

후처리

  1. stirringThe reaction solution was then stirred on a 90° C. oil bath for 6 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe resulting yellowish brown oily material (0.7456 g) was purified by silica gel column chromatography (Kiesegel 60, 60 g, chloroform/methanol= 15/1)
  5. customto obtain the objective compound (VI-2) (0.7076 g; yield: 72.3%) as an orange oily material

출처 및 근거

ORD 기록
ord-2a890baf6db44087adb63b22e3b17308
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05401736

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