2-Butanamine, 3,3-dimethyl- → 3-(3,5-Dimethoxyphenylamino)-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile

HRID 279113

Reaction equation

HRID 279113 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](SC)=[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])[C:14]#[N:15])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:22][CH:23]([NH2:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([NH:28][CH:23]([CH3:22])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])[C:14]#[N:15])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 701502363-(3,5-Dimethoxyphenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 498242313-(3,5-Dimethoxyphenylamino)-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile

Procedure

3-(3,5-dimethoxyphenylamino)-2-methanesulfonyl-3-methylsulfany-2-propenenitrile (0.263 g, 0.8 mmol) was stirred in 1,2,2-trimethylpropylamine (1 ml) for 17 h at 75° C. under nitrogen. Work-up as described in Example 17, 2) gave the title compound as a syrup, 262 mg (86%). 1H NMR (200 MHz, CDCl3): δ=0.85 (s, 9H), 1.01 (d, 3H), 3.12 (s, 3H), 3.26 (m, 1H), 3.78 (s, 6H), 6.25 (d, 2H), 6.35 (t, 1H); EI SP/MS: 381 (M+).

Sources & evidence

ORD record
ord-b85a597f1d5f4f2a91294c8dbe8ca5aa
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Linked notes

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