Methanol → HCID 90407942, compound

HRID 2277445Notes

Reaction equation

HRID 2277445 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([C:10]3[N:14]([CH3:15])[CH:13]=[N:12][C:11]=3[C:16]3[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][N:17]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[CH3:25]O>S(=O)(=O)(O)O>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:10]3[N:14]([CH3:15])[CH:13]=[N:12][C:11]=3[C:16]3[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][N:17]=3)=[CH:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 90407490HCID 90407490, compound

Product 1

HCID 90407942HCID 90407942, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a mixture of 2-[5-(4-cyclopropylphenyl)-1-methyl-1H-imidazol-4-yl]pyridine-4-carboxylic acid (26 mg, 0.08 mmol, Example 7) in MeOH (5 mL) was added 3 drops of concentrated sulfuric acid. The reaction mixture was heated to reflux for 1 hr. It was then concentrated, separated between water and ethyl acetate. Organic layer dried and concentrated to give the title compound as light pink solid (25 mg, 94%). 1H NMR (400 MHz, DMSO-d6): δ 0.77 (2H, m), 1.02 (2H, m), 2.02 (1H, m), 3.54 (3H, s), 3.85 (3H, s), 7.22 (2H, d&s, J=7.8 Hz), 7.36 (2H, d&s, J=8.1 Hz), 7.64 (1H, d, J=4.4 Hz), 7.98 (1H, s), 8.51 (1H, s), 8.63 (1H, s). [M+H] Calc'd for C20H19N3O2, 334. Found, 334.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hr
  3. concentrationIt was then concentrated
  4. customseparated between water and ethyl acetate
  5. customOrganic layer dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-68db30972be44dce931a1db67a623b01
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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