N-Iodosuccinimide → HCID 86717498, compound

HRID 712045Notes

Reaction equation

HRID 712045 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[N:8][C:7]3[CH:10]=[CH:11][S:12][C:6]=3[N:5]2[CH:13]=1.[I:14]N1C(=O)CCC1=O>C(Cl)Cl>[I:14][C:13]1[N:5]2[C:6]3[S:12][CH:11]=[CH:10][C:7]=3[N:8]=[CH:9][C:4]2=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86717499HCID 86717499, compound

Product 1

HCID 86717498HCID 86717498, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 7-methylimidazo[1,2-a]thieno[3,2-e]pyrazine (30 mg, 0.16 mmol), and N-iodosuccinimide (39 mg, 0.17 mmol) in methylene chloride (1.2 mL) was stirred at 25° C. for 16 h. The product was purified by prep-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (15 mg, 30%). LCMS calculated for C9H7IN3S (M+H)+: m/z=315.9. Found: 316.0. 1H NMR (CDCl3, 400 MHz) δ 8.89 (1H, s), 7.55 (1H, d, J=5.6 Hz), 7.35 (1H, d, J=5.6 Hz), 2.55 (3H, s) ppm.

Workup

  1. customThe product was purified by prep-HPLC (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-be73606ccab04fe480b9f2edcb9ab78c
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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