2-Butanamine, 3,3-dimethyl- → 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile

HRID 840235Notes

Reaction equation

HRID 840235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11](=[C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)SC)[C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:26][CH:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:28]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11](=[C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[NH:26][CH:27]([CH3:28])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 701506282-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 701503332-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrileYield 25%

Procedure

2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile (0.300 g, 0.6 mmol) was stirred in 2-amino-3,3-dimethylbutane (1 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 concentrated. The residue was trituated with ether to afford a white crystalline substance which was further purified by flash chromatography (SiO2) using heptane/ethyl acetate (1:1) to yield 85 mg(25%) of the title compound. Mp 80-82° C. 1H NMR (200 MHz, CDCl3): δ=0.90 (s, 9H), 1.02 (d, 3H), 3.02 (m, 1H), 7.27 (s, 2H), 7.47 (d, 2H), 7.51 (d,2H), 7.81 (d, 2H);

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed twice with 1N aqueous HCl, once with brine
  4. dry with materialThe organic phase was dried (sodium sulphate)
  5. concentrationconcentrated
  6. customto afford a white crystalline substance which
  7. customwas further purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-38168424809a486597b52af22bcdbb7a
Source dataset
uspto-grants-2002_04
Patent number
US06365609B1

Reaction notes

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