Aluminium lithium hydride → HCID 68312830, compound

HRID 1530580Notes

Reaction equation

HRID 1530580 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[C:16](OC)=[O:17])[C:12]1[N:8]([CH:9]=[C:10]([C:20]3[N:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[CH:22][N:21]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH2:16][OH:17])[C:12]1[N:8]([CH:9]=[C:10]([C:20]3[N:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[CH:22][N:21]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68313065methyl 12-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-13-carboxylate

Product 1

HCID 68312830HCID 68312830, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 12-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-13-carboxylate (100 mg, 0.272 mmol) in THF (10 mL) was added LiAlH4 (52 mg, 1.37 mmol). The mixture was heated to reflux for 2 h. After cooling to room temperature, the reaction was quenched with a piece of ice cube. The solid was filtered, washed with EtOAc (3×5 mL). The combined filtrate was concentrated to give {12-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca 1(14),2,4,10,12-pentaen-13-yl}methanol (92 mg, 100% yield), which was directly used in the next step without further purification. LCMS (ESI) m/z: 340.2 [M+H+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customthe reaction was quenched with a piece of ice cube
  4. filtrationThe solid was filtered
  5. washwashed with EtOAc (3×5 mL)
  6. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-5eaae856ca9e44028a7964f1c0c09c36
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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