Water → HCID 22672614, compound

HRID 1369562Notes

Reaction equation

HRID 1369562 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

lithium aluminum 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-2a2e52c45c744148a0a1e9ef75a83cc0
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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