Sodium Chloride → HCID 68431510, compound

HRID 2092067Notes

Reaction equation

HRID 2092067 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=O)[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30].O1CCCC1.B.[Cl-].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][CH2:10][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:28])[CH3:29])[C@H:22]1[CH3:30]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2723981Borane;tetrahydrofuranHCID 68430690HCID 68430690, compound

Product 1

HCID 68431510HCID 68431510, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)acetamide (35 mg, 0.073 mmol) in N,N-dimethylformamide (1 mL) was mixed with a borane tetrahydrofuran complex (1.13 M in tetrahydrofuran, 78 μL, 0.088 mmol) under cooling with ice and stirred at room temperature for 5.5 hours. After completion of the reaction, the reaction solution was mixed with saturated aqueous sodium chloride and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give the desired product (32 mg, 92% yield).

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-56ede104a36847a7a370983c6c25c9ad
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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