1,2-Dimethoxyethane → HCID 66770720, compound

HRID 1256261Notes

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]([F:19])[CH:15]=[CH:14][C:13]=2[C:12]2=[N:20][N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:22]([NH:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[C:11]2[N:10]=1.COCCOC.[S:44](N)([NH2:47])(=[O:46])=[O:45]>O>[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]([F:19])[CH:15]=[CH:14][C:13]=2[C:12]2=[N:20][N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:22]([NH:23][CH:24]3[CH2:25][CH2:26][N:27]([S:44]([NH2:47])(=[O:46])=[O:45])[CH2:28][CH2:29]3)=[C:11]2[N:10]=1

Participants

Conditions

Temperature: 150 °C

Procedure

180 mg of 5-(2,6-difluorophenyl)-7-fluoro-N-(piperidin-4-yl)-2-([2-(trimethylsilyl)ethoxy]methyl}-2H-pyrazolo[4,3-c]isoquinolin-3-amine, 2 ml of DME and 41 mg of sulphamide are mixed and microwave-heated at 150° C. for 1 h. The mixture is poured into water, extracted with AcOEt, washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated under RP. The product is purified by flash chromatography on silica gel (15-40 μm), eluting with a DCM/methanol/aqueous ammonia mixture (95/05/0.5 by vol.), to give 183 mg of 4-{[5-(2,6-difluorophenyl)-7-fluoro-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-pyrazolo[4,3-c]isoquinolin-3-yl]amino}piperidine-1-sulphonamide (yellow solid). LC-MS-DAD-ELSD: 607=(M+H).

Workup

extractionextracted with AcOEt
washwashed with saturated NaCl solution
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under RP
customThe product is purified by flash chromatography on silica gel (15-40 μm)
washeluting with a DCM/methanol/aqueous ammonia mixture (95/05/0.5 by vol.)

Sources & evidence

ORD record: ord-58617b9231d446e480e08f4b34a54127
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461175B2

Reaction notes

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