Borane → HCID 86700326, compound

HRID 879505Notes

Reaction equation

HRID 879505 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]3[C:16](=O)[NH:15][CH2:14][CH2:13][N:12]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.B>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]3[CH2:16][NH:15][CH2:14][CH2:13][N:12]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 86700325HCID 86700325, compound

Product 1

HCID 86700326HCID 86700326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

To the solution of tert-butyl 2-(1-methyl-1H-indazol-5-yl)-3-oxopiperazine-1-carboxylate (10 mg) in THF (0.5 mL) at 0° C. was added borane in THF (1.0 N, 1 mL) slowly. The mixture was heated at 55° C. for 3 hours, and was cooled. The reaction was quenched with methanol (1 mL), and was stirred for 30 minutes. The mixture was diluted with ethyl acetate, and was made basic with 1 N sodium hydroxide solution. The organic phase was separated, and was washed with water and brine, and was dried with sodium sulfate. Concentration gave tert-butyl 2-(1-methyl-1H-indazol-5-yl)piperazine-1-carboxylate. LCMS-ESI+: calc'd for C17H25N4O2: 317.2 (M+H+); Found: 317.0 (M+H+).

Workup

  1. temperaturewas cooled
  2. customThe reaction was quenched with methanol (1 mL)
  3. additionThe mixture was diluted with ethyl acetate
  4. customThe organic phase was separated
  5. washwas washed with water and brine
  6. dry with materialwas dried with sodium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-3d0d55a0282e4b9b94953cb66d2685d0
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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