2-Butanamine, 3,3-dimethyl- → 2-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile

HRID 279133Notes

Reaction equation

HRID 279133 reaction equation
[CH:1]([S:4]([C:7](=[C:10]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)SC)[C:8]#[N:9])(=[O:6])=[O:5])([CH3:3])[CH3:2].[NH2:22][CH:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:24]>>[CH:1]([S:4]([C:7](=[C:10]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[NH:22][CH:23]([CH3:24])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:8]#[N:9])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 701495792-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 701501352-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrileYield 80%

Procedure

2-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-methylsulfanyl-2-propenenitrile(0.500 g, 1.53 mmol) was stirred in 2-amino-3,3-dimethylbutane (2 ml) for 48 h at 100° C. under nitrogen in a sealed flask. The reaction mixture was concentrated and the residue dissolved in dichloromethane,washed twice with 1N aqueous HCl, once with brine, and once with water. The organic phase was dried (sodium sulphate) and evaporated to afford 450 mg (80%) of the title compound as white crystals. Mp 59-62 ° C.1H NMR (200 MHz, CDCl3): δ=0.84 (s, 9H), 0.96 (d, 3H), 1.40 (d, 6H), 3.00-3.33 (m, 2H), 3.82 (s, 3H), 6.70 (dd, 1H), 6.81 (dd, 1H), 7.31 (dd, 1H), 7.73-7.94 (m, 1H) 8.95 (br s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in dichloromethane,washed twice with 1N aqueous HCl, once with brine
  3. dry with materialThe organic phase was dried (sodium sulphate)
  4. customevaporated

Sources & evidence

ORD record
ord-5dfe87926a754a52a7d81f5165ba29f2
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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