Lithium borohydride → HCID 57785900, compound

HRID 1399216Notes

Reaction equation

HRID 1399216 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24](OC)=[O:25])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:16]3[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][N:17]=3)[CH2:12][CH2:13][CH2:14][CH2:15][N:7]21.[BH4-].[Li+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:16]4[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][N:17]=4)[CH2:12][CH2:13][CH2:14][CH2:15][N:7]3[C:6]=2[C:5]([CH2:24][OH:25])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 57785806HCID 57785806, compound

Product 1

HCID 57785900HCID 57785900, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl 10-chloro-1-(3,5-dichloropyridin-2-yl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole-7-carboxylate (426 mg, 1.00 mmol) in tetrahydrofuran (10 mL) was added lithium borohydride (54.5 mg, 2.50 mmol) at 0° C. After being stirred for 30 h at room temperature, the reaction mixture was diluted with ethyl acetate, quenched with aqueous ammonium chloride, washed with water and brine, dried over sodium sulfate, filtrated, and concentrated in vacuo to get the title compound as colorless solid (376 mg, 0.946 mmol, 95%).

Workup

  1. customquenched with aqueous ammonium chloride
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-991885e091a744af979b44f46fc2799d
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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