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

HRID 527863Notes

Reaction equation

HRID 527863 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][C:27]([CH:29]1[CH2:31][CH2:30]1)=[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][C:27]([CH:29]1[CH2:31][CH2:30]1)=[O:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 43133642N-(3-bromopropyl)cyclopropanecarboxamideHCID 178508696HCID 178508696, compound

Product 1

HCID 66562879N-(3-(6-Amino-8-((5-iodo-2,3-dihydrobenzofuran-6-yl)thio)-9H-purin-9-yl)propyl)cyclopropanecarboxamideYield 37.3%

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)cyclopropanecarboxamide (39 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 WS61 as a white solid (12 mg, 35%). 1H NMR (600 MHz, CDCl3): δ 8.30 (s, 1H), 7.57 (s, 1H), 7.16 (m, 1H), 6.55 (s, 1H), 5.67 (br s, 2H), 4.50 (t, J=8.8 Hz, 2H), 4.22 (t, J=6.3 Hz, 2H), 3.13 (t, J=8.6 Hz, 2H), 3.01-3.07 (m, 2H), 1.80-1.86 (m, 2H), 1.38-1.44 (m, 1H), 0.87-0.93 (m, 2H), 0.67-0.72 (m, 2H); HRMS (ESI) m/z [M+H]+ calcd. for C20H22IN6O2S, 537.0570. found 537.0567.

Workup

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

Sources & evidence

ORD record
ord-cd2b82fa5f9049bc8c338b5aa161b2da
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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