HCID 178490934, compound → HCID 178513740, compound

HRID 2239874Notes

Reaction equation

HRID 2239874 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([N:21](CC3C=CC(OC)=CC=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]3[N:13]([C:15]([C:18]([NH2:20])=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1>FC(F)(F)C(O)=O>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:12]3[N:13]([C:15]([C:18]([NH2:20])=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 178490934HCID 178490934, compound

Product 1

HCID 178513740HCID 178513740, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

Crude 6-((trans)-4-aminocyclohexylamino)-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carboxamide from 1b was suspended in trifluoracetic acid (1 mL) and heated to 50° C. for 2 h. The mixture was cooled to room temperature and the trifluoractic acid was evaporated under a stream of nitrogen. The residue was suspended in methanol, filtered to remove solids and purified by prep HPLC to provide 2.1 mg of the titled compound as a TFA salt. MS m/e 366 (M+1); 1H NMR (MeOH, δ) 8.1 (1H, s), 7.46 (2H, t, J=8 Hz), 7.39 (2H, d, J=8 Hz), 7.23 (1H, t, J=8 Hz), 6.31 (1H, s), 3.62 (1H, m), 3.17 (1H, m), 2.30 (2H, m), 2.13, (2H, m), 1.55 (2H, m), 1.42 (2H, m).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe trifluoractic acid was evaporated under a stream of nitrogen
  3. filtrationfiltered
  4. customto remove solids
  5. custompurified by prep HPLC

Sources & evidence

ORD record
ord-fd5e974bfacd443e862706ddabc7fdca
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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