Methanol → HCID 22672562, compound

HRID 1369591Notes

Reaction equation

HRID 1369591 reaction equation
[C:1]([C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:12]([NH:13][CH2:14][C:15]3[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=3C)[C:7]2=[N:6][C:5]=1[CH3:23])(=[O:3])[CH3:2].[CH3:24]O.[BH4-].[Na+]>O1CCCC1>[CH3:21][C:20]1[C:19]([CH3:24])=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:14][NH:13][C:12]1[C:7]2[N:8]([C:4]([CH:1]([OH:3])[CH3:2])=[C:5]([CH3:23])[N:6]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydride2×HCID 22672593HCID 22672593, compound

Product 1

HCID 22672562HCID 22672562, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-acetyl-8-(2,6-dimethylbenzylamino)-2-methylimidazo[1,2-a]pyridine (500 mg, 1.63 mmol) and methanol (20 ml) was sodium borohydride (62 mg, 1.63 mmol) added in portions. Tetrahydrofuran was added and the mixture stirred for 1 hour. TLC showed starting material and sodium borohydride (62 mg, 1.63 mmol) was added and the mixture stirred for 1.5 hour. The solvent was removed under reduced pressure and to the residue, methylene chloride and water was added. pH was adjusted to pH=3 with hydrogen chloride (conc.) and thereafter alkaline with sodium bicarbonate. The methylene choride layer was separated washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was treated with ethanol/ethyl acetate and after filtration (410 mg, 81%).

Workup

  1. additionadded in portions
  2. additionwas added
  3. stirringthe mixture stirred for 1.5 hour
  4. customThe solvent was removed under reduced pressure and to the residue, methylene chloride and water
  5. additionwas added
  6. customThe methylene choride layer was separated
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. additionThe residue was treated with ethanol/ethyl acetate
  11. filtrationafter filtration (410 mg, 81%)

Sources & evidence

ORD record
ord-c676553e6ce24536985728e5accf5599
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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