Cesium carbonate → tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)propylcarbamate

HRID 79283Notes

Reaction equation

HRID 79283 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[N:26]=2)[N:4]=1)[CH3:2].CS(O[CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.C(OCC)(=O)C.CO>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[N:26]=[C:27]([O:31][CH2:37][CH2:38][CH2:39][NH:40][C:41](=[O:42])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH:28]=[CH:29][CH:30]=2)[N:4]=1)[CH3:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 114141093-((Tert-butoxycarbonyl)amino)propyl methanesulfonateHCID 178437935HCID 178437935, compound

Product 1

HCID 67261867tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)propylcarbamateYield 25%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
82.5 °C

Procedure

To a solution of N-(3-ethyl-1-((6-hydroxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (50 mg, 0.121 mmol) (Prepared as in Example 17, Step A) and 3-(tert-butoxycarbonylamino)propyl methanesulfonate (107 mg, 0.422 mmol) in N,N-dimethylacetamide (2.0 mL) was added cesium carbonate (79.0 mg, 0.242 mmol). The mixture was heated at 80-85° C. for 90 minutes. The mixture was allowed to cool and diluted with ethyl acetate and methanol. The suspension was filtered and concentrated under a stream of nitrogen. The material was purified using preparative thin layer chromatography on silica, eluting with 5% methanol and 1% triethylamine in ethyl acetate to give the product (17.2 mg).

Workup

  1. temperatureto cool
  2. filtrationThe suspension was filtered
  3. concentrationconcentrated under a stream of nitrogen
  4. customThe material was purified
  5. washeluting with 5% methanol and 1% triethylamine in ethyl acetate

Sources & evidence

ORD record
ord-5b585db0896b4136bcc7ee9cd7b317eb
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…