Chlorosuccinimide → HCID 11652695, compound

HRID 2369241Notes

Reaction equation

HRID 2369241 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[NH:19][C:18]4[C:13](=[N:14][C:15]([F:21])=[N:16][C:17]=4[NH2:20])[N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C1C(=O)N([Cl:29])C(=O)C1>CN(C=O)C>[F:21][C:15]1[N:14]=[C:13]2[C:18]([NH:19][C:11]([CH2:10][C:8]3[C:7]([Cl:29])=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)=[N:12]2)=[C:17]([NH2:20])[N:16]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11601676HCID 11601676, compound

Product 1

HCID 11652695HCID 11652695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-Benzo[1,3]dioxol-5-ylmethyl-2-fluoroadenine (20 mg, 0.07 mmol), NCS (35.6 mg, 0.27 mmol) in anhydrous DMF (0.4 mL) was stirred at room temperature for 2.5 h. Following solvent removal, the product (11 mg, 48.8%) was collected through silica gel column purification (CHCl3:EtOAc at 9:1 to 5:5). 1H NMR (400 MHz, DMSO-d6) 7.40 (bs, 2H), 6.97 (s, 1H), 6.89 (s, 2H), 5.97 (s, 2H), 4.04 (s, 2H); MS m/z 322.1 (M+H)+.

Workup

  1. customFollowing solvent removal
  2. customthe product (11 mg, 48.8%) was collected through silica gel column purification (CHCl3:EtOAc at 9:1 to 5:5)

Sources & evidence

ORD record
ord-6c82f57ef7b14bc18e79666fc7b62f75
Source dataset
uspto-grants-2014_04
Patent number
US08703942B2

Reaction notes

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