Dimethylformamide → HCID 70855604, compound

HRID 527859Notes

Reaction equation

HRID 527859 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][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].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][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 10513201HCID 10513201, compoundHCID 178509024HCID 178509024, compound

Product 1

HCID 70855604HCID 70855604, compoundYield 18%

Procedure

To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (74 mg, 0.18 mmol) in DMF (2 mL) was added N-(3-bromopropyl)pivalamide (80 mg, 0.36 mmol) and Cs2CO3 (117 mg, 0.36 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 WS45 as a white solid (18 mg, 18%). 1H NMR (500 MHz, CDCl3): δ 8.23 (s, 1H), 7.45 (br s, 1H), 7.19 (s, 1H), 6.88 (s, 1H), 5.93 (s, 2H), 5.69 (br s, 2H), 4.20 (t, J=6.1 Hz, 2H), 3.00 (m, 2H), 1.80 (m, 2H), 1.21 (s, 9H); HRMS (ESI) m/z [M+H]+ calcd. for C20H24IN6O3S, 555.0675. found 555.0681.

Workup

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

Sources & evidence

ORD record
ord-0a0656a04a5c432180cac552f188c66b
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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