Trifluoroacetic acid → 6-(3-Amino-1,2-benzisoxazol-6-yl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

HRID 2239886Notes

Reaction equation

HRID 2239886 reaction equation
COC1C=CC(C[N:8]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[C:10]3[N:11]([CH:25]=[CH:26][N:27]=3)[N:12]=[C:13]([C:15]3[CH:24]=[CH:23][C:18]4[C:19]([NH2:22])=[N:20][O:21][C:17]=4[CH:16]=3)[CH:14]=2)=CC=1.C(O)(C(F)(F)F)=O>>[NH2:22][C:19]1[C:18]2[CH:23]=[CH:24][C:15]([C:13]3[CH:14]=[C:9]([NH:8][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:10]4[N:11]([CH:25]=[CH:26][N:27]=4)[N:12]=3)=[CH:16][C:17]=2[O:21][N:20]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684838686-(8-((4-Methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine

Product 1

HCID 593044476-(3-Amino-1,2-benzisoxazol-6-yl)-N-phenylimidazo[1,2-b]pyridazin-8-amineYield 17%

Procedure

To a solution of 6-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine from (1b) was added TFA (1 mL) and the solution stirred at RT for 1 hour. The reaction solution was concentrated in vacuo and then diluted with methanol and purified by preparative HPLC to provide the titled compound (3.90 mg, 17%). 1H NMR (500 MHz, CD3OD) δ ppm 8.26 (1H, s), 7.92 (1H, s), 7.86 (1H, d, J=8.6 Hz), 7.80 (1H, d, J=8.25 Hz), 7.52 (4H, m), 7.35 (1H, t, J=7.15 Hz), 7.27 (1H, s). LC/MS, m/e 343 (M+1). HPLC Rt, 2.52 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additiondiluted with methanol
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3dbcdd4c53b04debb75d72f9aedce49c
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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