3-Bromo-6-chloro-7-methylimidazo[1,2-b]pyridazine → (3-Bromo-7-methyl-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine

HRID 870697Notes

Reaction equation

HRID 870697 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[C:9]([CH3:11])=[CH:10][C:5]2=[N:4][CH:3]=1>C(N)CCC>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:4][CH2:5][CH2:10][CH2:9][CH3:8])[C:9]([CH3:11])=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 1

HCID 593802983-Bromo-6-chloro-7-methylimidazo[1,2-b]pyridazine

Product 1

HCID 86696400(3-Bromo-7-methyl-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Conditions

Temperature
160 °C

Procedure

To the 3-bromo-6-chloro-7-methyl-imidazo[1,2-b]pyridazine from Part B was added n-BuNH2 (10 ml). The mixture was heated in a microwave at 160° C. for 60 min (30+30 min.). The mixture was concentrated and the residue was subjected to ISCO (40 g column, hexane 3 min., 0-100% EtOAc in hexane over 25 min. the EtOAc 10 min.) to five the titled compound (348 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.97 (t, J=7.39 Hz, 3H) 1.29-1.50 (m, 2H) 1.61-1.71 (m, 2H) 2.14 (s, 3H) 3.44 (q, J=6.62 Hz, 2H) 4.39 (br. s., 1H) 7.34 (s, 1H) 7.37 (s, 1H). LRMS (ESI) m/z 283 and 285 [(M+H)]+, calc'd for C11H15BrN4: 283.17.

Workup

  1. concentrationThe mixture was concentrated
  2. custom40 g column, hexane 3 min., 0-100% EtOAc in hexane
  3. customover 25 min.
  4. customthe EtOAc 10 min.

Sources & evidence

ORD record
ord-4a47ef3ec2a04a829ff6d0453b224ba4
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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