Dimethylformamide → HCID 11594638, compound

HRID 2356974Notes

Reaction equation

HRID 2356974 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]([C:20]#[N:21])[CH2:15][CH2:16][O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C>C1COCC1>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]([CH2:20][NH2:21])[CH2:15][CH2:16][O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 58668701HCID 58668701, compound

Product 1

HCID 11594638HCID 11594638, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Benzenesulfonyl-chroman-4-carbonitrile (300 mg, 1 mmol) was dissolved in 10 mL THF, and 237 ul (2.5 mmol) of BH3.DMF was added. The reaction mixture was stirred for one hour at room temperature, and then heated to 80° C. for twenty minutes. The reaction mixture was then cooled, quenched by addition of methanol, and diluted with water. The aqueous mixture was extrated with EtOAc. The organic phase was dried over MgSO4, and solvent was removed under reduced pressure to yield 95 mg (31%) of C-(7-benzenesulfonyl-chroman-4-yl)-methylamine. MS: 304 (M+H)+. This product was dissolved in 2N HCl/EtOH and recrystallized by addition of Et2O to afford 52 mg of the corresponding hydrochloride salt. Mp: 246.8-249.8° C.

Workup

  1. temperatureheated to 80° C. for twenty minutes
  2. temperatureThe reaction mixture was then cooled
  3. customquenched by addition of methanol
  4. additiondiluted with water
  5. dry with materialThe organic phase was dried over MgSO4, and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-49368d0fece44937845dbd3dbaf67902
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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