Cesium carbonate → N-(3-(6-Amino-8-((5-iodo-2,3-dihydrobenzofuran-6-yl)thio)-9H-purin-9-yl)propyl)-2-methylpropane-2-sulfinamide

HRID 527864Notes

Reaction equation

HRID 527864 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][CH2:7][C:6]=2[CH:10]=1.Br[CH2:23][CH2:24][CH2:25][NH:26][S:27]([C:29]([CH3:32])([CH3:31])[CH3:30])=[O:28].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[CH2:7][CH2:8][O:9][C:5]=3[CH:4]=1)[N:13]2[CH2:23][CH2:24][CH2:25][NH:26][S:27]([C:29]([CH3:32])([CH3:31])[CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 88996323N-(3-bromopropyl)-2-methlpropane-2-sulfinamideHCID 178508696HCID 178508696, compound

Product 1

HCID 90073190N-(3-(6-Amino-8-((5-iodo-2,3-dihydrobenzofuran-6-yl)thio)-9H-purin-9-yl)propyl)-2-methylpropane-2-sulfinamideYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-((5-iodo-2,3-dihydrobenzofuran-6-yl)thio)-9H-purin-6-amine (26 mg, 0.06 mmol) in DMF (1.5 mL) was added N-(3-bromopropyl)-2-methlpropane-2-sulfinamide (49 mg, 0.18 mmol) and Cs2CO3 (41 mg, 0.12 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS62 as a white solid (11 mg, 30%). 1H NMR (600 MHz, CDCl3): δ 8.33 (s, 1H), 7.66 (s, 1H), 6.61 (s, 1H), 5.85 (br s, 2H), 4.84 (t, J=6.7 Hz, 1H), 4.59 (t, J=8.7 Hz, 2H), 4.37-4.44 (m, 1H), 4.29-4.35 (m, 1H), 3.22 (t, J=8.5 Hz, 2H), 3.09-3.16 (m, 1H), 2.95-3.02 (m, 1H), 2.06-2.15 (m, 1H), 1.93-2.05 (m, 1H), 1.29 (s, 9H); HRMS (ESI) m/z [M+H]+ calcd. for C20H26IN6O2S2, 573.0603. found 573.0620.

Workup

  1. customcondensed under vacuum
  2. customthe residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1)

Sources & evidence

ORD record
ord-9b98961a3adb44d499a1cb7838cf78f0
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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