Triethylamine → HCID 58524135, compound

HRID 536435Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](=NO)[C:9]2[C:13]=1[N:12]([CH3:14])[NH:11][C:10]=2C)=[O:4].ClN1C(=[O:24])CCC1=O.[Cl:26][C:27]1[CH:32]=[C:31]([C:33]([C:35]([F:38])([F:37])[F:36])=[CH2:34])[CH:30]=[C:29]([Cl:39])[CH:28]=1.C([N:42]([CH2:45]C)CC)C>CN(C)C=O.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:45]2[CH2:34][C:33]([C:31]3[CH:32]=[C:27]([Cl:26])[CH:28]=[C:29]([Cl:39])[CH:30]=3)([C:35]([F:36])([F:37])[F:38])[O:24][N:42]=2)=[C:9]2[C:13]=1[N:12]([CH3:14])[N:11]=[CH:10]2)=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-(hydroxyimino-methyl-1-methyl-1H-indazole-7-carboxylic acid methyl ester (1.4 g) in dimethyl formamide (50 ml) was treated with N-chlorosuccinimide (0.85 g) and stirred at 50° C. for 3 h under nitrogen atmosphere. Then reaction mixture was cooled to room temperature and treated with 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.43 g) (prepared according to WO 2005/085216) and triethylamine (0.8 ml), stirred at room temperature for 16 h under nitrogen atmosphere, and treated with water (50 ml). The solid appeared was filtered and purified by column chromatograph (hexane/ethyl acetate 20:80) to give 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1-methyl-1H-indazole-7-carboxylic acid methyl ester (1.1 g). 1H-NMR (400 MHz, DMSO): 8.47 (s, 1H), 7.95 (d, 1H), 7.82 (d, 1H), 7.68 (s, 2H), 7.51 (d, 1H), 4.52 (dd, 2H), 4.09 (s, 3H), 3.97 (s, 3H). LC-MS (methanol): m/z=471 (M+H).

Workup

customThen reaction mixture
temperaturewas cooled to room temperature
stirringstirred at room temperature for 16 h under nitrogen atmosphere
filtrationThe solid appeared was filtered
custompurified by column chromatograph (hexane/ethyl acetate 20:80)

Sources & evidence

ORD record: ord-9c38717f9c814da9b5ea4e46071ad7a8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859592B2

Reaction notes

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