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 1609479Notes

Reaction equation

HRID 1609479 reaction equation
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]

Participants

5

Reactant 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

Product 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 esterYield 72.3%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-2a890baf6db44087adb63b22e3b17308
Source dataset
uspto-grants-1995_03
Patent number
US05401736

Reaction notes

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