Hexane → (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide

HRID 2184901Notes

Reaction equation

HRID 2184901 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Al](C)C.[CH3:26]CCCCC.[C:32]([C:34]1[CH:35]=[C:36](/[CH:40]=[CH:41]/[C:42]([O:44]CC)=O)[CH:37]=[CH:38][CH:39]=1)#[N:33]>ClCCl>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:42](=[O:44])/[CH:41]=[C:40](/[C:36]2[CH:37]=[CH:38][CH:39]=[C:34]([C:32]#[N:33])[CH:35]=2)\[CH3:26])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 5373498Ethyl (2E)-3-(3-cyanophenyl)-2-propenoateHCID 10804475N-tert-butyl-4'-aminobiphenyl-2-sulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 22458345(2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamideYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2′-tert-butylaminosulfonyl-4-amino-[1,1′]-biphenyl (79 mg, 0.26 mmol) in 4 ml anhydrous dichloromethane was added a solution of 2M trimethylaluminum in hexane (0.39 ml, 0.78 mmol). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (E) 3-(3-cyanophenyl)-2-propenoate (56 mg, 0.26 mmol) in 1 ml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with 5 ml 1N HCl after which an additional 10 ml dichloromethane was added. Organic layer was washed with 2×20 ml water, dried over magnesium sulfate, filtered and concentrated to give the (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90 mg, 72%) as an off-white powder which was sufficiently pure to be used without further purification.

Workup

  1. customReaction
  2. additionwas added
  3. customReaction
  4. customReaction
  5. customwas quenched with 5 ml 1N HCl after which an additional 10 ml dichloromethane
  6. additionwas added
  7. washOrganic layer was washed with 2×20 ml water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ac0b50b0879d401c8d5ea9c8c73df122
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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