Pyridine → HCID 68826778, compound

HRID 1723921Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[C:13]2[S:24][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][C:14]=2[N:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1.N1C=CC=C[CH:30]=1>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[C:13]3[S:24][C:23]([C:25]([O:27][CH2:28][CH3:30])=[O:26])=[CH:22][C:14]=3[N:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=2)=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 4-fluorobenzoyl chloride (0.106 mol, 12.7 mL) in 50 ml of anhydrous dichlorometane was added dropwise to an ice-cold suspension of 1-ethyl 5-methyl 3-amino-thieno[3,2-c]pyrazole-1,5-dicarboxylate (0.071 mol, 19.1 g) in 100 mL of anhydrous dichlorometane and 114.0 mL of pyridine (1.412 mol). The resulting suspension was stirred at 5° C., for 5 hours. The crude was concentrated under vacuum and diluted with dichloromethane. The organic layer was washed with hydrochloric acid 1. N, sodium hydroxide 1 N, brine and dried over Na2SO4. The filtrate was evaporated to dryness to give a yellow solid, which was purified by flash chromatography, over silica gel, using hexane/ethyl acetate (4:1) as eluent, to afford the title compound as a pale yellow solid (19.6 g, 68%).

Workup

concentrationThe crude was concentrated under vacuum
additiondiluted with dichloromethane
washThe organic layer was washed with hydrochloric acid 1
dry with materialN, sodium hydroxide 1 N, brine and dried over Na2SO4
customThe filtrate was evaporated to dryness
customto give a yellow solid, which
customwas purified by flash chromatography, over silica gel

Sources & evidence

ORD record: ord-8b6bafcde38c4f9bb344509f40531242
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485661B2

Reaction notes

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