Water → HCID 57917454, compound

HRID 69202Notes

Reaction equation

FC(F)(F)C([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([CH:14]([OH:30])[C:15]3[N:19]4[N:20]=[C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)[CH:22]=[CH:23][C:18]4=[N:17][CH:16]=3)=[CH:10][N:9]2[CH:31]=1)=O.C([O-])([O-])=O.[K+].[K+].O>C1COCC1.CO>[NH2:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:15]3[N:19]4[N:20]=[C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)[CH:22]=[CH:23][C:18]4=[N:17][CH:16]=3)[OH:30])=[CH:10][N:9]2[CH:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(rac)-2,2,2-Trifluoro-N-(6-{hydroxy-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methyl}-imidazo[1,2-a]pyridin-2-yl)-acetamide (Example 153, 120 mg, 0.263 mmol) was dissolved in THF/MeOH 1:1 (2 mL). K2CO3 was added (363 mg, 2.63 mmol) with water (1 mL) and the RM was heated over night at 90° C. After concentration under reduced pressure, the residue was purified by flash chromatography (CombiFlash® Companion System®, with 12 g RediSep® silica gel column, DCM/MeOH=8:2->DCM/MeOH/H2O/ammonia=80:19:0.5: 0.5) to afford the title compound (MH+=361, 1H NMR in DMSO-d6: .8.5 (s, 1H); 8.4 (s, 1H); 8.1 (s, 1H); 8.0 (d, 1H); 7.6 (s, 1H); 7.5 (d, 1H), 7.1 (q, 2H), 7.0 (s, 1H); 6.2 (s, 2H); 5.0 (s, 2H); 3.9 (s, 3H)).

Workup

concentrationAfter concentration under reduced pressure
customthe residue was purified by flash chromatography (CombiFlash® Companion System®, with 12 g RediSep® silica gel column, DCM/MeOH=8:2->DCM/MeOH/H2O/ammonia=80:19:0.5: 0.5)

Sources & evidence

ORD record: ord-f1872d827cf9481e8974085e8e793ea0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822468B2

Reaction notes

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