N-Iodosuccinimide → 4-Iodo-2-(thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-7-amine

HRID 389553Notes

Reaction equation

HRID 389553 reaction equation
[S:1]1[C:5]2=[CH:6][N:7]=[N:8][CH:9]=[C:4]2[C:3]([C:10]2[O:19][C:13]3=[C:14]([NH2:18])[N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=[CH:2]1.[I:20]N1C(=O)CCC1=O>CN(C)C=O>[I:20][C:17]1[CH:16]=[N:15][C:14]([NH2:18])=[C:13]2[O:19][C:10]([C:3]3[C:4]4[C:5](=[CH:6][N:7]=[N:8][CH:9]=4)[S:1][CH:2]=3)=[CH:11][C:12]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 667606692-(Thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-7-amine

Product 1

HCID 667608664-Iodo-2-(thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-7-amineYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-7-amine (30.0 mg, 0.112 mmol) and N-iodosuccinimide (101.6 mg, 0.4516 mmol) in N,N-dimethylformamide (2 mL) was stirred at 40° C. for 45 min. The reaction was removed from the heat and 1.0 M aqueous sodium thiosulfate solution (2 mL) was added. The crude mixture was concentrated in vacuo. The residue was then suspended in water and the fine solid was filtered off and dried, giving 39.0 mg (88%) of the title compound as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 10.48 (d, J=1.52 Hz, 1H), 10.02 (d, J=1.52 Hz, 1H), 9.04 (s, 1H), 7.96 (s, 1H), 7.45 (s, 1H), 6.89 (s, 2H); MS (ESI): 395.07 [M+H]+; HPLC: tR=2.83 min.

Workup

  1. customThe reaction was removed from the
  2. temperatureheat
  3. addition1.0 M aqueous sodium thiosulfate solution (2 mL) was added
  4. concentrationThe crude mixture was concentrated in vacuo
  5. filtrationthe fine solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-b3c16b5f70b54274942e2fe7b6398f26
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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