Acetonitrile → N-{2-[7-(2-Benzo[d]isoxazol-3-yl-ethyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethyl}-4-cyano-benzenesulfonamide

HRID 1992401Notes

Reaction equation

Cl.Cl.[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH2:15][CH2:16][N:17]2[CH2:24][CH:23]3[O:25][CH:19]([CH2:20][NH:21][CH2:22]3)[CH2:18]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4].[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[C:28]([CH2:35][CH2:36]OS(C)(=O)=O)=[N:27]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[C:28]([CH2:35][CH2:36][N:21]2[CH2:22][CH:23]3[O:25][CH:19]([CH2:18][N:17]([CH2:16][CH2:15][NH:14][S:11]([C:8]4[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[CH:6][CH:7]=4)(=[O:13])=[O:12])[CH2:24]3)[CH2:20]2)=[N:27]1

Participants

Conditions

Temperature: 160 °C

Procedure

To 4-cyano-N-[2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethyl]-benzenesulfonamide dihydrochloride (0.123 g, 0.30 mmol, from prep E above), methanesulfonic acid 2-benzo[d]isoxazol-3-yl-ethyl ester (0.076 g, 0.315 mmol, from prep AD above) and potassium carbonate (0.145 g, 1.05 mmol; from Prep ) was added acetonitrile (4 mL) and water (0.1 mL). The mixture was heated by microwave irradiation (10 minutes, 160° C.) and was then filtered and evaporated. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 60 mg (41.5%) of the title compound.

Workup

filtrationwas then filtered
customevaporated
customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-306104b712024a7d9f6d77effa2d58a0
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648985B2

Reaction notes

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