Dimethylformamide → HCID 86713735, compound

HRID 527861Notes

Reaction equation

HRID 527861 reaction equation
[I:1][C:2]1[C:3]([S:11][C:12]2[N:20]=[C:19]3[C:15]([N:16]=[CH:17][NH:18]3)=[C:14](N)[N:13]=2)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.Br[CH2:23][CH2:24][CH2:25][NH:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28].C([O-])([O-])=O.[Cs+].[Cs+].C[N:40](C=O)C>>[NH2:40][C:15]1[N:16]=[CH:17][N:18]=[C:19]2[C:14]=1[N:13]=[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:20]2[CH2:23][CH2:24][CH2:25][NH:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 60865661HCID 60865661, compoundHCID 178509024HCID 178509024, compound

Product 1

HCID 86713735HCID 86713735, compoundYield 20%

Procedure

To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (118 mg, 0.28 mmol) in DMF (2 mL) was added N-(3-bromopropyl)propane-2-sulfonamide (350 mg, 1.4 mmol) and Cs2CO3 (188 mg, 0.56 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 WS48 as a white solid (33 mg, 20%). 1H NMR (500 MHz, CDCl3/MeOH-d4): δ 8.20 (s, 1H), 7.41 (s, 1H), 7.09 (s, 1H), 6.08 (s, 2H), 4.35 (t, J=7.0 Hz, 2H), 3.10-3.22 (m, 3H), 2.07 (m, 2H), 1.37 (d, J=6.9 Hz, 6H); 13C NMR (125 MHz, CDCl3/MeOH-d4): δ 158.4, 156.1, 155.1, 153.9, 153.5, 151.8, 129.2, 123.5, 123.3, 117.9, 106.6, 98.3, 57.0, 44.8, 43.9, 34.3, 20.2; HRMS (ESI) m/z calcd. for C18H22IN6O4S2, 577.0189. found 577.0193.

Workup

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

Sources & evidence

ORD record
ord-9cb036d92c704d1ca5fbc0407517ed8a
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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