Trifluoroacetic acid → 6-(3-Amino-1,2-benzisoxazol-5-yl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

HRID 2239883Notes

Reaction equation

HRID 2239883 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:16]=[CH:17][C:18]4[O:22][N:21]=[C:20]([NH2:23])[C:19]=4[CH:24]=3)[CH:14]=2)=CC=1.CCOC1C=CC(N)=CC=1.C(O)(C(F)(F)F)=O>>[NH2:23][C:20]1[C:19]2[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]=[CH:17][C:18]=2[O:22][N:21]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90764-EthoxyanilineHCID 68478268HCID 68478268, compound

Product 1

HCID 593044526-(3-Amino-1,2-benzisoxazol-5-yl)-N-phenylimidazo[1,2-b]pyridazin-8-amineYield 70%

Procedure

To a solution of 5-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine from (1c) was added TFA (1 mL) and the solution stirred at RT for 1 hour. The reaction solution was concentrated in vacuo, diluted with methanol and purified by preparative HPLC to provide the titled compound (13.20 mg, 70%). 1H NMR (500 MHz, CD3OD) δ ppm 8.3 (1H, s), 8.21 (1H, d=2.2 Hz), 8.11 (1H, m), 7.97 (1H, m), 7.52 (4H, m), 7.3 (1H, m), 7.1 (1H, m), 7.07 (1H, d, J=8.8 Hz). LC/MS, m/e 343 (M+1). HPLC Rt, 2.63 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-41d8c4f4b1df4f23a507942c83063294
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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