Lithium borohydride → HCID 86729408, compound

HRID 521235Notes

Reaction equation

HRID 521235 reaction equation
[C:1]([C:4]1[C:5]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[N:6][N:7]([C:9]2([CH2:25][C:26]#[N:27])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:24])([CH3:23])[C:19](OC)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH:8]=1)(=[O:3])[NH2:2].[Li+].[BH4-]>C1COCC1.CCOC(C)=O.[Cl-].[NH4+]>[C:1]([C:4]1[C:5]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)=[N:6][N:7]([C:9]2([CH2:25][C:26]#[N:27])[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:24])([CH3:23])[CH2:19][OH:20])=[O:16])[CH2:13][CH2:14]2)[CH:8]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 2

HCID 4148881Lithium borohydrideHCID 86729409HCID 86729409, compound

Product 1

HCID 86729408HCID 86729408, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1-methoxy-2-methyl-1-oxopropan-2-yl 4-{4-carbamoyl-3-[(4-fluorophenyl)amino]-1H-pyrazol-1-yl}-4-(cyanomethyl)piperidine-1-carboxylate (70 mg, 0.14 mmol) in THF (1.9 mL) at ambient temperature was added LiBH4 (25 mg, 1.2 mmol). The mixture was allowed to stir at ambient temperature for 3 hours. The mixture was then diluted with EtOAc and saturated aqueous ammonium chloride. The organic layer was separated, washed with water, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-10% MeOH/EtOAc) to afford the title compound, Example 29.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by MPLC on silica gel (
  7. washa gradient elution of 0-10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-5b8be23d7a0942cfb7e2943f493e48e5
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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