Sodium Iodide → HCID 131728653, compound

HRID 1363022Notes

Reaction equation

CS(O[CH2:6][CH2:7][CH2:8][S:9]([CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:11])=[O:10])(=O)=O.[CH2:17]([C:21]1[CH:22]=[C:23]2[C:28](=[C:29]([O:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)[CH2:18][CH2:19][CH3:20].[I-].[Na+].[C:40](=O)([O-:42])[OH:41].[Na+]>CN(C=O)C.CO>[CH:40]([OH:42])=[O:41].[CH2:17]([C:21]1[CH:22]=[C:23]2[C:28](=[C:29]([O:31][CH:32]3[CH2:33][CH2:34][N:35]([CH2:6][CH2:7][CH2:8][S:9]([CH:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)(=[O:11])=[O:10])[CH2:36][CH2:37]3)[CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)[CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 3-(cyclopentylsulfonyl)propyl methanesulfonate (for example, as prepared for Intermediate 25) (0.081 g, 0.3 mmol), 6-butyl-8-(4-piperidinyloxy)quinoline (for example, as prepared for Intermediate 4) (0.102 g, 0.360 mmol), sodium iodide (40 mg, 0.3 mmol) and sodium hydrogen carbonate (200 mg, 2.39 mmol) in dry DMF (2 ml) was heated in a Smith Creator™ microwave oven at 150° C. for 15 min. The reaction mixture was applied to an SCX-2 cartridge (20 g), preconditioned with methanol. The cartridge was washed with methanol (4×25 ml) and then eluted with 10% aqueous 0.88 s.g. ammonia in methanol (4×25 ml). The solvents were removed in vacuo and the resultant residue purified by MDAP to afford the title compound (53 mg): LCMS RT=2.81 min; ES+ve m/z 459 (M+H)+

Workup

washThe cartridge was washed with methanol (4×25 ml)
washeluted with 10% aqueous 0.88 s
customThe solvents were removed in vacuo
customthe resultant residue purified by MDAP

Sources & evidence

ORD record: ord-0703e46410774cc2941940a9ec253bf6
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884114B2

Reaction notes

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