Methanol → HCID 178511625, compound

HRID 1943483Notes

Reaction equation

HRID 1943483 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:28](CC3C=CC(OC)=CC=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1.CO.O>C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 178490938HCID 178490938, compound

Product 1

HCID 178511625HCID 178511625, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

The solid from 62B was dissolved in TFA and heated to 70° C. for 1 h and then cooled to room temperature and purified by preparative HPLC (Phenomenex Axia Luna 5 micron 30×100 mm) to obtain the pure product 6-((trans-4-aminocyclohexyl)amino)-N-(2-fluoro-4-pyridinyl)-8-(2-pyridinylamino)imidazo[1,2-b]pyridazine-3-carboxamide (23 mg, 0.050 mmol, 41.9% yield) HPLC Rt=1.542 minutes (Phenomenex Luna 5 micron C18 4.6×30 mm: 0 to 100 B in 2 min with 1 min hold time, Flow rate=5 mL/min, detection at 254 nm, Solvent A: 10% methanol/90% water/0.1% TFA; Solvent B: 10% water/90% methanol/0.1% TFA). [M+H]=462.17.

Workup

  1. temperaturecooled to room temperature
  2. custompurified by preparative HPLC (Phenomenex Axia Luna 5 micron 30×100 mm)

Sources & evidence

ORD record
ord-1367e5b114f94913b5cd9759f6c364fe
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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