Sodium Bicarbonate → HCID 68415693, compound

HRID 1800677Notes

Reaction equation

HRID 1800677 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH:19]=O)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH3:19])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86646069HCID 86646069, compound

Product 1

HCID 68415693HCID 68415693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-[3-(formylamino)phenyl]benzamide (405 mg, 1.32 mmol) produced in Example D3(ii) in tetrahydrofuran (15 mL) was added borane dimethylsulfide complex (361 μL, 3.42 mmol), and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (20 mL), and the mixture was extracted with ethyl acetate (20 mL, 10 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give 3-(1-cyano-1-methylethyl)-N-[3-(methylamino)phenyl]benzamide as a brown oil. The obtained compound was used for the next reaction without further purification.

Workup

  1. additionwas added borane dimethylsulfide complex (361 μL, 3.42 mmol)
  2. extractionthe mixture was extracted with ethyl acetate (20 mL, 10 mL)
  3. washThe combined organic layer was washed with saturated brine (5 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-75168f24c47744a4bf5bc1601903eb9b
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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