Cyclobutylamine → 3-(3,5-Bis(trifluoromethyl)phenylamino)-3-cyclobutylamino-2-isopropylsulfonyl-2-propenenitrile

HRID 279131Notes

Reaction equation

HRID 279131 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([NH:13][C:14](SC)=[C:15]([S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:28]1([NH2:32])[CH2:31][CH2:30][CH2:29]1>>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([NH:13][C:14]([NH:32][CH:28]2[CH2:31][CH2:30][CH2:29]2)=[C:15]([S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[C:16]#[N:17])[CH:4]=[C:3]([C:2]([F:26])([F:1])[F:27])[CH:8]=1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 865837393-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 865841123-(3,5-Bis(trifluoromethyl)phenylamino)-3-cyclobutylamino-2-isopropylsulfonyl-2-propenenitrileYield 89%

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile (0.500 g, 1.16 mmol) was stirred in cyclobutylamine (2 ml) for 24 h at 80° C. under nitrogen in a sealed flask. Work up as described in Example 40, 2) gave 470 mg (89%) of the title compound as white crystals. Mp 148-150° C. 1H NMR (200 MHz, CDCl3): δ=1.38 (d, 6H), 1.49-1.85 (m, 2H), 2.02 (q, 4H), 3.26 (heptet, 1H), 3.53-3.77 (m, 1H), 7.46 (s, 2H), 7.64 (s, 1H), 7.96-8.14 (m, 1H), 9.17 (brs, 1H)

Sources & evidence

ORD record
ord-d140a788bbf549b398cf346a225c312d
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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