Hydrochloric Acid → HCID 71547822, compound

HRID 1497430Notes

Reaction equation

HRID 1497430 reaction equation
[N:1]1([CH:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[Li+].[OH-].Cl>C1COCC1.O>[N:1]1([CH:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:25]=[CH:24][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71547821HCID 71547821, compound

Product 1

HCID 71547822HCID 71547822, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)benzoate (25 mg, 0.07 mmol; prepared as described in Example 5) in THF (2 mL) and water (1 mL) was added LiOH (6 mg, 0.14 mmol) at rt and the reaction was stirred at rt for about 4 h. The reaction mixture was neutralized with 1N HCl (pH=6) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by prep TLC using 5% methanol in DCM to provide 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)benzoic acid as an off white solid (12 mg, 54.5% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.92 (s, 1H), 8.14 (dd, 1H), 8.01 (d, 2H), 7.83 (d, 3H), 7.40 (d, 1H), 7.31 (s, 1H), 6.90 (s, 1H), 5.39 (s, 1H), 2.34-2.19 (m, 2H), 0.81 (t, 3H), LC-MS m/z calcd for [M+H]+ 308.13. found 308.1.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organic extracts were washed with brine solution (10 mL)
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto obtain crude product
  6. customThe crude product was purified by prep TLC

Sources & evidence

ORD record
ord-5cf5d248aa7d4350b6d6245fb745608c
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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