Dimethylformamide → HCID 86713734, compound

HRID 527860Notes

Reaction equation

HRID 527860 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:31])[CH:28]([CH3:30])[CH3:29].C([O-])([O-])=O.[Cs+].[Cs+].C[N:39](C=O)C>>[NH2:39][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:31])[CH:28]([CH3:30])[CH3:29]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 15324182HCID 15324182, compoundHCID 178509024HCID 178509024, compound

Product 1

HCID 86713734HCID 86713734, compoundYield 34%

Procedure

To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (50 mg, 0.12 mmol) in DMF (2 mL) was added N-(3-bromopropyl)isobutyramide (50 mg, 0.24 mmol) and Cs2CO3 (78 mg, 0.24 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 WS46 as a white solid (22 mg, 34%). 1H NMR (500 MHz, CDCl3/MeOH-d4): δ 8.22 (s, 1H), 7.61 (br s, 1H), 7.41 (s, 1H), 7.08 (s, 1H), 6.07 (s, 2H), 4.27 (m, 2H), 3.21 (m, 2H), 2.45 (s, 1H), 2.02 (m, 2H), 1.19 (d, J=6.9 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C19H22IN6O3S, 541.0519. found 541.0508.

Workup

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

Sources & evidence

ORD record
ord-05473eaa9b014ef3b8b42247bd601871
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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