Triethylamine → 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(5-cyclopropyl-2-methyl-2H-pyrazol-3-ylamino)-2-propenenitrile

HRID 840219Notes

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.C(N(CC)CC)C.[NH2:39][C:40]1[N:44]([CH3:45])[N:43]=[C:42]([CH:46]2[CH2:48][CH2:47]2)[CH:41]=1>C(#N)C>[F:10][C:9]([F:11])([F:12])[C:7]1[CH:6]=[C:5]([NH:13][C:14]([NH:39][C:40]2[N:44]([CH3:45])[N:43]=[C:42]([CH:46]3[CH2:48][CH2:47]3)[CH:41]=2)=[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:4]=[C:3]([C:2]([F:30])([F:31])[F:1])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(3,5-bis(trifluoromethyl)phenylamino)-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.300 g, 0.6 mmol) in dry acetonitrile (1.0 ml), triethylamine (0.100 ml, 0.7 mmol) and 5-amino-3-cyclopropyl-1-methyl pyrazole (0.100 g, 0.7 mmol) were added. The reaction mixture was stirred for 41 h at 80° C. under nitrogen and then concentrated. The residue was worked up as described in Example 17.2) to give 90 mg (25%) of the title compound. 1H NMR (200 MHz, CDCl3): δ=0.7 (m, 2H), 0.9 (m, 2H), 1.85 (m, 1H), 3.5 (s, 3H), 5.3 (s, 1H), 5.4 (s, 1H), 5.85 (s, 1H), 7.28 (s, 2H), 7.53 (d, 2H), 7.63 (s, 1H), 7.8 (d, 2H); EI SP/MS: 589 (M+).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-d4acfe05305843c69b0f4e855ccd92d4
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365609B1

Reaction notes

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