Ammonium Chloride → HCID 66900150, compound

HRID 1394655Notes

Reaction equation

HRID 1394655 reaction equation
C[O:2][C:3](=[O:30])[CH:4]=[CH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[C:17]([CH:24]([CH3:26])[CH3:25])[C:16]=3[O:27][CH2:28][CH3:29])=[CH:13][N:14]=2)[CH:11]=1.[Cl-].[NH4+]>CO.[OH-].[Na+]>[CH2:28]([O:27][C:16]1[C:17]([CH:24]([CH3:26])[CH3:25])=[CH:18][C:19]([CH:21]([CH3:23])[CH3:22])=[CH:20][C:15]=1[C:12]1[N:10]2[CH:11]=[C:6]([CH:5]=[CH:4][C:3]([OH:30])=[O:2])[CH:7]=[CH:8][C:9]2=[N:14][CH:13]=1)[CH3:29]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 69217560HCID 69217560, compound

Product 1

HCID 66900150HCID 66900150, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-[3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridin-6-yl]-acrylic acid methyl ester (288 mg, 0.71 mmol) in MeOH (5 ml) and 1N NaOH (5 ml) was heated to 40° C. for 2 h. The reaction was cooled, then brought to pH 7.5 with solid ammonium chloride and extracted with ethyl acetate (2×10 mL). The combined organic layers were then dried over MgSO4 and evaporated to a residue. The residue was purified by silica gel chromatography (10% MeOH in dichloromethane) to give 3-[3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridin-6-yl]-acrylic acid as a white solid (65 mg, 23%). 1H NMR (250 MHz, CDCl3): δ 8.02 (s, 1H), 7.64 (m, 2H), 7.57 (d, 1H, J=7.5),7.39 (m, 1H), 7.17 (d, 1H), J=1.2), 7.04 (d, 1H, J=1.2), 6.35 (d, 1H, J=16.9), 3.37 (m, 1H), 3.26 (q, 2H, J=7.2), 2.88 (m, 1H), 1.26 (s, 3H), 1.23 (s, 6H), 1.20 (s, 3H), 0.72 (t, 3H, J=7.2). MS [EI+] 393 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialThe combined organic layers were then dried over MgSO4
  4. customevaporated to a residue
  5. customThe residue was purified by silica gel chromatography (10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-8115925f78b947b8adeac4c008ea469d
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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