Aluminium lithium hydride → HCID 56960125, compound

HRID 1749610Notes

Reaction equation

HRID 1749610 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[C:5]2[CH:18]=[C:19]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:20]=[C:21]([C:22](O)=[O:23])[C:4]=2[N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[C:5]2[CH:18]=[C:19]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:20]=[C:21]([CH2:22][OH:23])[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 569595312-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carboxylic acid

Product 1

HCID 56960125HCID 56960125, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the mixture of 2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carboxylic acid, prepared as described in Example 20 (70 mg, 0.174 mmol) in Tetrahydrofuran (THF) (5 mL) was added in LiAlH4 (19.85 mg, 0.523 mmol) at 0° C. and the reaction mixture was stirred at rt for 1 h. Then LiAlH4 (19.85 mg, 0.523 mmol) was added in and the reaction mixture was stirred at rt for another hour. The reaction mixture was cooled to 0° C. and quenched with water (0.04 ml), NaOH (15%, 0.04 ml) then water (0.12 ml). After the resultant mixture was stirred at room temperature for 2 h, anhydrous MgSO4 was added and the reaction mixture was filtered through celite and washed with EtOAc. Evaporation of the solvent gave the crude product. The crude product was purified on a silica column (0-4% MeOH/DCM) to give the solid (12 mg, 17%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.38 (s, 3H), 2.91-3.05 (m, 4H), 3.64-3.74 (m, 4H), 4.89 (d, J=5.56 Hz, 2H), 5.12 (t, J=5.81 Hz, 1H), 5.95 (s, 2H), 6.33 (d, J=6.82 Hz, 1H), 6.81 (d, J=2.02 Hz, 1H), 6.97 (d, J=1.77 Hz, 1H), 7.34 (t, J=7.71 Hz, 1H), 7.54-7.74 (m, 2H), 7.85 (d, J=8.08 Hz, 1H), 8.01 (d, J=7.58 Hz, 1H), 8.25 (d, 1H). MS(ES+) m/z 388.0 [M+H]+.

Workup

  1. customprepared
  2. stirringwas stirred at rt for another hour
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customquenched with water (0.04 ml), NaOH (15%, 0.04 ml)
  5. stirringAfter the resultant mixture was stirred at room temperature for 2 h
  6. additionanhydrous MgSO4 was added
  7. filtrationthe reaction mixture was filtered through celite
  8. washwashed with EtOAc
  9. customEvaporation of the solvent
  10. customgave the crude product
  11. customThe crude product was purified on a silica column (0-4% MeOH/DCM)

Sources & evidence

ORD record
ord-0526d8816dca49c0b9914a639bdb294b
Source dataset
uspto-grants-2015_10
Patent number
US09156797B2

Reaction notes

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