Dimethylformamide → HCID 66562687, compound

HRID 527867Notes

Reaction equation

HRID 527867 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.[C:22]([NH:26][S:27]([CH2:30][CH2:31]Cl)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23].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[CH2:31][CH2:30][S:27]([NH:26][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:29])=[O:28]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 87205876HCID 87205876, compoundHCID 178509024HCID 178509024, compound

Product 1

HCID 66562687HCID 66562687, compoundYield 13%

Procedure

To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (56 mg, 0.13 mmol) in DMF (2 mL) was added N-t-butyl-2-chloroethanesulfonamide (50 mg, 0.25 mmol) and Cs2CO3 (88 mg, 0.27 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 WS47 as a white solid (10 mg, 13%). 1H NMR (500 MHz, CDCl3/MeOH-d4): δ 8.22 (s, 1H), 7.39 (s, 1H), 7.08 (s, 1H), 6.06 (s, 2H), 4.69 (t, J=7.0 Hz, 2H), 3.57 (t, J=7.1 Hz, 2H), 1.35 (s, 9H); 13C NMR (125 MHz, CDCl3/MeOH-d4): δ 158.3, 156.4, 155.1, 153.9, 153.4, 151.5, 129.2, 123.5, 123.3, 117.8, 106.6, 98.1, 58.5, 57.3, 42.7, 33.8; HRMS (ESI) m/z [M+H]+ calcd. for C18H22IN6O4S2, 577.0189. found 577.0217.

Workup

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

Sources & evidence

ORD record
ord-9448a31bef5b4f1b80d21683cf770b44
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

Loading…