N-Iodosuccinimide → HCID 86696450, compound

HRID 870742Notes

Reaction equation

HRID 870742 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([CH:20]=[CH:21][N:22]=3)[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:23]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([I:23])=[CH:21][N:22]=3)[N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86696451HCID 86696451, compound

Product 1

HCID 86696450HCID 86696450, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-imidazo[1,2-b]pyridazin-6-yl-piperazine-1-carboxylic acid tert-butyl ester (3.6 g, 11.8 mmol) and N-iodosuccinimide [516-12-1] (3.1 g, 13.1 mmol) in DMF (120 mL) was stirred under N2 blanket at ambient temperature for 2 h then partitioned between 5% (w/v) aqueous sodium metabisulfite and ethyl acetate. The organic phase was washed with brine, dried (CaSO4), evaporated, and crystallized from ethyl acetate/heptane to provide a white crystalline powder, mp. 203-204° C. (dec.). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43 (s, 9H) 3.45-3.51 (m, 4H) 3.51-3.58 (m, 4H) 7.19 (d, J=9.92 Hz, 1H) 7.61 (s, 1H) 7.85 (d, J=9.92 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ ppm 27.89, 45.06, 70.52, 78.95, 110.55, 125.66, 137.28, 137.71, 153.73, 154.88. LRMS (ESI) m/z 430.0 (M+H)]+, calc'd for C15H20IN5O2: 429.26.

Workup

  1. customthen partitioned between 5% (w/v) aqueous sodium metabisulfite and ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (CaSO4)
  4. customevaporated
  5. customcrystallized from ethyl acetate/heptane
  6. customto provide a white crystalline powder, mp. 203-204° C. (dec.)

Sources & evidence

ORD record
ord-25754b0a1468446ba803f4b0e5369cca
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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