Sodium Iodide → HCID 15603142, compound

HRID 550556Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.CS(O[CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[N:30]([CH3:31])[C:29]([S:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)=[N:28][N:27]=1)(=O)=O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+].[Cl:50]CCl>CN(C)C=O>[ClH:50].[CH:34]1([CH2:33][S:32][C:29]2[N:30]([CH3:31])[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][N:11]3[CH2:12][C@H:13]4[C@:9]([C:6]5[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=5)([CH2:14]4)[CH2:10]3)=[N:27][N:28]=2)[CH2:35][CH2:36]1

Participants

Conditions

Temperature: 60 °C

Procedure

(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (70 mg) and 4-{5-[(cyclopropylmethyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl}butyl methanesulfonate (70 mg) were dissolved in dimethylformamide (0.6 ml). Sodium Iodide (12 mg) and potassium carbonate (35 mg) were added. Reaction was heated at 60° C. for 20 h. Dichloromethane and NaHCO3 saturated solution were added. Solvent was removed, under reduced pressure, from organic phase. Crude was purified by silica column to give the free base of the title compound (5.5 mg). To a solution of this compound in DCM (0.5 mL), HCl 1N in diethylether (0.012 mL) was added and the solvent removed under reduced pressure to give the title compound as a slightly hygroscopic solid. (6.7 mg).

Workup

customReaction
customSolvent was removed, under reduced pressure, from organic phase
customCrude was purified by silica column

Sources & evidence

ORD record: ord-1e6181f3d51b4c7c88d52611e61a10df
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947683B2

Reaction notes

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