Hexane → HCID 22458356, compound

HRID 2184924Notes

Reaction equation

HRID 2184924 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.CCCCCC.[C:32]([C:34]1[CH:35]=[C:36]([C:40]2[CH2:44][CH2:43][CH2:42][C:41]=2[C:45](OCC)=[O:46])[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:45]([C:41]2[CH2:42][CH2:43][CH2:44][C:40]=2[C:36]2[CH:37]=[CH:38][CH:39]=[C:34]([C:32]#[N:33])[CH:35]=2)=[O:46])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 10804475N-tert-butyl-4'-aminobiphenyl-2-sulfonamideHCID 16682925TrimethylaluminumHCID 22458359HCID 22458359, compound

Product 1

HCID 22458356HCID 22458356, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2′-tert-butylaminosulfonyl-4-amino-[1,1′]-biphenyl (60 mg, 0.197 mmol) in 4 ml anhydrous dichloromethane was added a solution of 2M trimethylaluminum in hexane (0.3 ml, 0.59 mmol). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl 2-(3-cyanophenyl)-1-cyclopentene-1-carboxylate (48 mg, 0.197 mmol) in lml anhydrous dichloromethane. Reaction was stirred at room temperature overnight. Reaction was quenched with 15 ml 1N HCl after which an additional 10 ml dichloromethane was added. Organic was washed with 2×20 ml water, dried over magnesium sulfate and concentrated to give N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl][2-(3-cyanophenyl)cyclopent-1-enyl]carboxamide (80 mg, 80%) as a white powder which was sufficiently pure to be used without further purification.

Workup

  1. customReaction
  2. customReaction
  3. customReaction
  4. customwas quenched with 15 ml 1N HCl after which an additional 10 ml dichloromethane
  5. additionwas added
  6. washOrganic was washed with 2×20 ml water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-930b13f888ac4e409574d773b3e579cf
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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