Dimethyl Sulfoxide → HCID 20484892, compound

HRID 647441Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[CH:5]=[C:4]([N:13]([C:15]2[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH3:14])[N:3]=1.[F-:29].[K+].[CH3:31][S:32](C)=O>C(Cl)Cl>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([N:13]([C:15]3[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=3)[CH3:14])[N:3]=[C:2]2[S:32][CH3:31])=[CH:7][CH:8]=1.[Cl:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([N:13]([C:15]3[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=3)[CH3:14])[N:3]=[C:2]2[F:29])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of ethyl 2-{4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (0.90 g), anhydrous potassium fluoride (1.50 g) and dry dimethyl sulfoxide (10 ml) was stirred at 160° C. for 48 hrs. The cooled mixture was dissolved in methylene chloride and washed repeatedly with water, then dried (MgSO4) and evaporated to give a crude, brown oil. Purification by column chromatography over silica gel (eluant: methylene chloride/hexane) gave Ethyl 2-{4-[N-(7-chloro-1-methylthioisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (0.060 g) as a yellow oil and ethyl 2-{4-[N-(7-chloro-1-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (0.180 g) as a yellow oil.

Workup

washwashed repeatedly with water
dry with materialdried (MgSO4)
customevaporated
customto give a crude, brown oil
customPurification by column chromatography over silica gel (eluant: methylene chloride/hexane)

Sources & evidence

ORD record: ord-165929d5b961407dba4d8172db1aecf6
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04409017

Reaction notes

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