Pyridine → 5-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

HRID 245638Notes

Reaction equation

[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]2[C:5]([C:6]([CH3:14])=[N:7][NH:8]2)=[CH:4][C:3]=1[Cl:15].[Cl:16][C:17]1[C:18]([N:23]2[C:27]([C:28](O)=O)=[CH:26][C:25]([C:31]([F:34])([F:33])[F:32])=[N:24]2)=[N:19][CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1.CS(Cl)(=O)=O>O1CCCC1>[Cl:15][C:3]1[CH:4]=[C:5]2[C:6]([CH3:14])=[N:7][NH:8][C:9]2=[C:10]2[C:2]=1[N:1]=[C:28]([C:27]1[N:23]([C:18]3[C:17]([Cl:16])=[CH:22][CH:21]=[CH:20][N:19]=3)[N:24]=[C:25]([C:31]([F:34])([F:32])[F:33])[CH:26]=1)[O:12][C:11]2=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 540 mg (2.39 mmol) of 6-amino-5-chloro-3-methyl-1H-indazole-7-carboxylic acid in 22 mL of anhydrous tetrahydrofuran at 10° C., is added 698 mg (2.39 mmol) of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid followed by 963 μL (11.97 mmol) of pyridine. Then the suspension is cooled to 0° C. and 748 μL (9.57 mmol) of methanesulfonyl chloride are added dropwise. The mixture is stirred at ambient temperature for 48 hours. Then the solvent is evaporated and the residue is taken-up with acetone. After filtration, the filtrate is evaporated in vacuo. The residue obtained is purified by flash chromatography (SiO2, heptane/ethyl acetate 1:2) and affords 810 mg (1.68 mmol, 70%) of the product as a solid; LC/MS:481/483 (M+H)+.

Workup

customThen the solvent is evaporated
filtrationAfter filtration
customthe filtrate is evaporated in vacuo
customThe residue obtained
customis purified by flash chromatography (SiO2, heptane/ethyl acetate 1:2)

Sources & evidence

ORD record: ord-0e4b67c8e190469d8f15672218795304
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658801B2

Reaction notes

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