2-Butanamine, 2-methyl- → HCID 86583735, compound

HRID 279107Notes

Reaction equation

HRID 279107 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14](SC)=[C:15]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:32][C:33]([NH2:37])([CH3:36])[CH2:34][CH3:35]>>[F:31][C:2]([F:30])([F:1])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:37][C:33]([CH3:36])([CH3:32])[CH2:34][CH3:35])=[C:15]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

3

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 865837313-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 86583735HCID 86583735, compoundYield 8%

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.300 g, 0.6 mmol) was stirred in 1,1-dimethylpropylamine (1 ml) for 40 h at 60° C. and for 43 h at 110° C. under nitrogen. The reaction mixture was concentrated and the residue dissolved in DCM, washed twice with 1N aqueous HCl and once with water. The organic phase was dried (sodium sulfate) and concentrated. The residue was purified by flash chromatography using from ethyl acetate/heptane 1:2 as eluent followed recrystallisation from ethyl acetate/heptane 1:2 to give 25 mg (8%) of the title compound. Mp 205-207° C. 1H NMR (200 MHz, CDCl3): δ=0.98 (t, 3H), 1.54 (s, 6H), 1.68 (q, 2H), 7.10 (s, 2H), 7.53 (d, 2H), 7.60 (s, 1H), 7.81 (d, 2H); EI SP/MS: 539 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in DCM
  3. washwashed twice with 1N aqueous HCl and once with water
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. customrecrystallisation from ethyl acetate/heptane 1:2

Sources & evidence

ORD record
ord-65c2bf7f7a874bbabc0864249422cc89
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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