Cyclopentylamine → 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-cyclopentylamino-2-propenenitrile

HRID 279130Notes

Reaction equation

HRID 279130 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([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1>>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:33][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:15]([S:18]([CH:21]([CH3:22])[CH3:23])(=[O:20])=[O:19])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 865837393-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 739865853-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-cyclopentylamino-2-propenenitrileYield 99%

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile (0.500 g, 1.16 mmol) was stirred in cyclopentylamine (2 ml) for 24 h at 80° C. under nitrogen in a sealed flask. Work up as described in Example 40, 2) gave 540 mg (99%) of the title compound as white crystals. Mp 172-173 ° C. 1H NMR (200 MHz, CDCl3): δ=1.41 (d, 6H), 1.40-1.57 (m, 4H), 1.74-1.93 (m, 4H), 3.25 (heptet, 1H), 3.56 (m, 1H), 7.54 (s, 2H), 7.67 (s, 1H), 7.94 (br s, 1H), 9.22 (br s, 1H)

Sources & evidence

ORD record
ord-65d992ad765247e49057f13c9aa5b3db
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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