1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl Chloride → 2-[1-(3-Chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-6-nitro-4H-3,1-benzoxazin-4-one

HRID 1983071Notes

Reaction equation

[CH3:1][C:2]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:4]2[C:5]([O:7][C:8](=O)[NH:9][C:3]=12)=[O:6].[Cl:17][C:18]1[C:19]([N:24]2[C:28](C(Cl)=O)=[CH:27][C:26]([C:32]([F:35])([F:34])[F:33])=[N:25]2)=[N:20][CH:21]=[CH:22][CH:23]=1>N1C=CC=CC=1>[Cl:17][C:18]1[C:19]([N:24]2[C:28]([C:8]3[O:7][C:5](=[O:6])[C:4]4[CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:2]([CH3:1])[C:3]=4[N:9]=3)=[CH:27][C:26]([C:32]([F:35])([F:33])[F:34])=[N:25]2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 505 mg (1.63 mmol) of the title material from Step A, 344 mg (1.55 mmoles) of 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride (which can be prepared according to Example 7) and 2 mL of pyridine was heated at 100° C. for 3 hours. The resulting mixture was cooled to 25° C. and partitioned between ethyl acetate and dilute aqueous HCl. The organic layer was washed three times with dilute aqueous HCl, dried over anhydrous magnesium sulfate and concentrated to give a brown solid that was used in the next step without further purification. 1H NMR (CDCl3): δ 8.86 (d, 1H), 8.60 (dd, 1H), 8.38 (d, 1H), 8.03 (dd, 1H), 7.59 (s, 1H), 1.95 (s, 3H).

Workup

temperatureThe resulting mixture was cooled to 25° C.
custompartitioned between ethyl acetate and dilute aqueous HCl
washThe organic layer was washed three times with dilute aqueous HCl
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customto give a brown solid that
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-a5692f41d4aa4586a3ac0d6c4e3dc5e1
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541377B2

Reaction notes

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