Water → HCID 22672614, compound

HRID 1006666Notes

Reaction equation

HRID 1006666 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:12]1[N:16]2[CH:17]=[CH:18][CH:19]=[C:20]([NH:21][CH2:22][C:23]3[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:30][O:31][CH3:32])[C:15]2=[N:14][C:13]=1[CH3:33])([O:9]CC)=O.O.[OH-].[Na+].O1CCC[CH2:38]1>>[CH3:33][C:13]1[N:14]=[C:15]2[C:20]([NH:21][CH2:22][C:23]3[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:30][O:31][CH3:32])=[CH:19][C:18]([CH3:38])=[CH:17][N:16]2[C:12]=1[CH2:7][OH:9]

Participants

6

Reactant 5

HCID 962Water2×HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22672587HCID 22672587, compound

Product 1

HCID 22672614HCID 22672614, compound

Procedure

Litium aluminium hydride (0.29 g, 7.7 mmol) was added to tetrahydrofuran (30 ml) and 3-carbethoxy-8-(2-methoxymethyl-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine (1.4 g, 3.8 mmol) dissolved in tetrahydrofuran (30 ml) was added dropwise during 80 min. at room temperature and stirred for 4 h. Water (0.29 ml) was added dropwise, followed by sodium hydroxide (15%, 0.29 ml) and finally 0.93 ml of water. After stirring 30 min. the solids were filtered off and washed thoroughly with tetrahydrofuran. The solvent was removed under reduced pressure and chromatography on silica gel (methylene chloride:methanol, 9:1) gave (0.97 g 75%) of the title compound as a white solid.

Workup

  1. additionwas added dropwise during 80 min. at room temperature
  2. stirringAfter stirring 30 min. the solids
  3. filtrationwere filtered off
  4. washwashed thoroughly with tetrahydrofuran
  5. customThe solvent was removed under reduced pressure and chromatography on silica gel (methylene chloride:methanol, 9:1)

Sources & evidence

ORD record
ord-7fc4ee52edd44ae8bf6dc2392cf127c0
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

Loading…