Cesium carbonate → HCID 86713732, compound

HRID 527853

Reaction equation

HRID 527853 reaction equation
[I:1][C:2]1[C:3]([S:11][C:12]2[NH:13][C:14]3[C:19]([N:20]=2)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=3)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.Br[CH2:23][CH2:24][NH:25][S:26]([C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:28])=[O:27].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:21][C:18]1[N:17]=[CH:16][N:15]=[C:14]2[C:19]=1[N:20]=[C:12]([S:11][C:3]1[C:2]([I:1])=[CH:10][C:6]3[O:7][CH2:8][O:9][C:5]=3[CH:4]=1)[N:13]2[CH2:23][CH2:24][NH:25][S:26]([C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 63688805HCID 63688805, compoundHCID 178508697HCID 178508697, compound

Product 1

HCID 86713732HCID 86713732, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio)-9H-purin-6-amine (30.4 mg, 0.07 mmol) in 3 mL of dry DMF was added 2-methyl-propane-2-sulfonic acid (2-bromo-ethyl)-amide (90 mg, 0.37 mmol) and Cs2CO3 (80 mg, 0.25 mmol). The resulting mixture was stirred at a temperature of about 25° C. for 3 hrs, condensed under reduced pressure and purified by flash chromatography to provide compound WS42 as pale yellow solid (17 mg, 41% yield).

Workup

  1. customcondensed under reduced pressure
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5553de24ce904237a87b522938062aea
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Linked notes

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