Ammonium Chloride → HCID 17954317, compound

HRID 1354168Notes

Reaction equation

HRID 1354168 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([OH:10])=[C:8]([CH2:11][CH2:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:6][N:5]2[C:26]=1[CH3:27].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([OH:10])=[C:8]([CH2:11][CH2:12][CH:13]([OH:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:6][N:5]2[C:26]=1[CH3:27]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 17954323HCID 17954323, compound

Product 1

HCID 17954317HCID 17954317, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2,3-dimethyl-8-hydroxy-7-(3′-oxo-3′-phenylpropyl)-imidazo[1,2-a]pyridine-6-carboxylate (714 mg, 1.95 mmol) in ethanol (20 ml) is treated with sodium borohydride (74 mg, 1.95 mmol). The reaction mixture is stirred for 2.75 hours at ambient temperature. At 0° C. saturated ammonium chloride solution (20 ml) is added. The solution is evaporated until most of the ethanol has been removed and is extracted with dichloromethane (3×20 ml). The combined organic phases are dried over sodium sulfate and are evaporated to dryness. A brownish foam (692 mg) is obtained which is purified by flash chromatography [silica gel, solvent system: dichloromethane/methanol=15:1 (v/v)]. The title compound (540 mg, 75%) is isolated as an almost colourless foam, 90% purity according to 1H NMR analysis.—1H NMR (CDCl3, 200 MHz): □=1.40 (t, 3 H), 2.13 (mc, 2 H), 2.40 (s, 3 H), 2.52 (s, 3 H), 3.26 (mc, 1 H), 3.50 (mc, 1H), 4.39 (q, 2 H), 4.61 (dd, 1 H), 7.24 (mc, 5 H), 7.95 (s, 1 H).

Workup

  1. customThe solution is evaporated until most of the ethanol
  2. customhas been removed
  3. extractionis extracted with dichloromethane (3×20 ml)
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customare evaporated to dryness

Sources & evidence

ORD record
ord-764383d57f56453985187253fae06d66
Source dataset
uspto-grants-2007_05
Patent number
US07223771B2

Reaction notes

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