Dimethylformamide → HCID 70855695, compound

HRID 527862Notes

Reaction equation

HRID 527862 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]([O:25][C:26]([CH3:35])([CH3:34])[C:27]([NH:29][CH2:30][CH2:31][CH2:32]Br)=[O:28])(=[O:24])[CH3:23].C([O-])([O-])=O.[Cs+].[Cs+].C[N:43](C=O)C>>[C:22]([O:25][C:26]([CH3:35])([CH3:34])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][N:20]1[C:12]([S:11][C:3]2[C:2]([I:1])=[CH:10][C:6]3[O:7][CH2:8][O:9][C:5]=3[CH:4]=2)=[N:13][C:14]2[C:19]1=[N:18][CH:17]=[N:16][C:15]=2[NH2:43])=[O:28])(=[O:24])[CH3:23]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 86713736HCID 86713736, compoundHCID 178509024HCID 178509024, compound

Product 1

HCID 70855695HCID 70855695, compoundYield 22%

Procedure

To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (59 mg, 0.14 mmol) in DMF (1.5 mL) was added 1-((3-bromopropyl)amino)-2-methyl-1-oxopropan-2-yl acetate (120 mg, 0.48 mmol) and Cs2CO3 (93 mg, 0.28 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 WS57 as a white solid (19 mg, 22%). 1H NMR (600 MHz, CDCl3): δ 8.23 (s, 1H), 7.90 (t, J=6.0 Hz, 1H), 7.26 (s, 1H), 6.85 (s, 1H), 5.95 (s, 2H), 5.54 (br s, 2H), 4.21 (t, J=5.9 Hz, 2H), 2.93-2.99 (m, 2H), 2.08 (s, 3H), 1.83-1.90 (m, 2H), 1.59 (s, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C21H24IN6O5S, 599.0574. found 599.0579.

Workup

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

Sources & evidence

ORD record
ord-0c7bd0f21d4f44bdb49ada65dcbd49aa
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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