Water → HCID 66773274, compound

HRID 1256231Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([I:19])[CH:15]=[CH:14][C:13]=2[C:12]2[NH:20][N:21]=[CH:22][C:11]=2[N:10]=1.[H-].[Na+].[CH3:25][N:26]([CH3:31])[S:27](Cl)(=[O:29])=[O:28].O>C1COCC1.CN(C=O)C>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([I:19])[CH:15]=[CH:14][C:13]=2[C:12]2[N:20]([S:27]([N:26]([CH3:31])[CH3:25])(=[O:29])=[O:28])[N:21]=[CH:22][C:11]=2[N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 250 ml three-necked flask equipped with a magnetic stirrer and an argon intake is charged with 4 g of 5-(2,6-difluorophenyl)-7-iodo-1H-pyrazolo[4,3-c]isoquinoline, prepared in step 6 of example 1, in 120 ml of THF and 3 ml of DMF. The mixture is cooled to 0° C. using an ice bath and then 952 mg of sodium hydride (60%) are added. After 15 min at 0° C., 1.3 ml of dimethylsulphamoyl chloride are added. After 16 h at RT, the mixture is poured into 300 ml of water and extracted with ethyl acetate. The organic phase is dried over MgSO4, filtered and concentrated under RP. The solid obtained is triturated in diisopropyl ether. The insoluble material is filtered off under RP and dried under vacuum to give 2.94 g of 5-(2,6-difluorophenyl)-7-iodo-N,N-dimethyl-1H-pyrazolo[4,3-c]isoquinoline-1-sulphonamide (beige solid). LC-MS-DAD-ELSD: 515(+)=(M+H)(+).

Workup

customA 250 ml three-necked flask equipped with a magnetic stirrer
waitAfter 16 h at RT
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over MgSO4
filtrationfiltered
concentrationconcentrated under RP
customThe solid obtained
customis triturated in diisopropyl ether
filtrationThe insoluble material is filtered off under RP
customdried under vacuum

Sources & evidence

ORD record: ord-b99b2d79949948dc98ed429e7f94f3b6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461175B2

Reaction notes

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