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

HRID 79281Notes

Reaction equation

HRID 79281 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][NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])(=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][NH:39][C:40](=[O:41])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH:28]=[CH:29][CH:30]=2)[N:4]=1)[CH3:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamateHCID 178437935HCID 178437935, compound

Product 1

HCID 67261301tert-butyl 2-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)ethylcarbamateYield 33%

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 (Example 17, Step A; 50 mg, 0.121 mmol) and 2-(tert-butoxycarbonylamino)ethyl methanesulfonate (71 mg, 0.297 mmol) in N,N-dimethylacetamide (2 mL) was added cesium carbonate (79.0 mg, 0.242 mmol). The mixture was heated to 80-85° C. for 90 minutes. After allowing to cool the mixture was diluted with ethyl acetate and methanol, 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 21.9 mg (33%).

Workup

  1. temperatureto cool the mixture
  2. filtrationfiltered
  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-ea546d2f4be440ffbad0d1ad6b2bbdb0
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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