Hydrochloric Acid → HCID 178442433, compound

HRID 1927689Notes

Reaction equation

HRID 1927689 reaction equation
[CH3:1][C:2]([CH3:27])([CH2:25][CH3:26])[CH2:3][C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[C:13]([C:23]#N)[CH:12]=2)[NH:7][CH:8]=1.Cl.[K].[OH-:30].[K+].C[OH:33]>>[CH3:1][C:2]([CH3:27])([CH2:25][CH3:26])[CH2:3][C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[C:13]([CH:12]=2)[C:23]([OH:33])=[O:30])[NH:7][CH:8]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 178442432HCID 178442432, compound

Product 1

HCID 178442433HCID 178442433, compound

Procedure

A mixture of 2-(4-{2-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}-2-cyanophenyl)pyridine (30 mg, 0.08 mmol) and 6N HCl (10 mL) was heated at reflux for 3 h. Upon cooling, the volatiles were removed, and the resulting residue was purified by flash column chromatography on silica gel eluting with 0-10% methanol/ammonium hydroxide mixture in methylene chloride the title compound, which was converted to the potassium salt with KOH (1 eq) in methanol. NMR (500 MHz, CD3OD) δ 8.53-8.51 (d, J=4.5 Hz, 1H), 7.81-7.77 (m, 1H), 7.63-7.61 (d, J=7.9 Hz, 1H), 7.49 (s, 1H), 7.43-7.42 (d, J=7.8 Hz, 1H), 7.33-7.30 (m, 1H), 7.13-7.11 (m, 1H), 6.96 (s, 1H), 3.22-3.19 (t, J=7.5 Hz, 2H), 3.10-3.07 (t, J=7.2 Hz, 2H), 2.44 (s, 2H), 1.23-1.16 (m, 2H), 0.85-0.82 (t, J=7.4 Hz, 3H), 0.79 (s, 6H); LC-MS: m/e 378 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureUpon cooling
  4. customthe volatiles were removed
  5. customthe resulting residue was purified by flash column chromatography on silica gel eluting with 0-10% methanol/ammonium hydroxide mixture in methylene chloride the title compound, which

Sources & evidence

ORD record
ord-f6e89841704b409d8490aba5b5e59b27
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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