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 1609479ノート

反応式

HRID 1609479 の反応式
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]

参加物

5

反応物 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

生成物 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 ester収率 72.3%

試薬・触媒・溶媒 1

HCID 9005Trimethyl orthoformate溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-2a890baf6db44087adb63b22e3b17308
出典データセット
uspto-grants-1995_03
特許番号
US05401736

反応ノート

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