Water → HCID 66665201, compound

HRID 872367Notes

Reaction equation

HRID 872367 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[C:19]([Cl:20])=[CH:18][C:17]([C:21]([NH2:23])=O)=[CH:16][N:15]4[C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.CCCP(O)(O)=O.O>C(OCC)(=O)C>[NH2:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:13]=[C:14]4[C:19]([Cl:20])=[CH:18][C:17]([C:21]#[N:23])=[CH:16][N:15]4[C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 204484Propylphosphonic acidHCID 66665309HCID 66665309, compound

Product 1

HCID 66665201HCID 66665201, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2-[4-(1-aminocyclobutyl)phenyl]-8-chloro-3-phenylimidazo[1,2-a]pyridine-6-carboxamide (see example 6-1, 100 mg, 0.17 mmol, 72% purity) and 1-propylphosphonic acid cyclic anhydride as 50%-solution in ethyl acetate (0.21 ml, 0.35 mmol) in 1.35 ml ethyl acetate were stirred at room temperature overnight. The reaction mixture was hydrolysed with water and extracted with ethyl acetate. The organic phase was filtered through a Whatman filter and the volatile components were removed by rotary evaporation. The crude material was purified by column chromatography (Snap cartridge, dichloromethane/ethanol 95/5->dichloromethane/ethanol 7/3) to give 11 mg of the title compound (16% overall yield).

Workup

  1. extractionextracted with ethyl acetate
  2. filtrationThe organic phase was filtered through a Whatman
  3. filtrationfilter
  4. customthe volatile components were removed by rotary evaporation
  5. customThe crude material was purified by column chromatography (Snap cartridge, dichloromethane/ethanol 95/5->dichloromethane/ethanol 7/3)

Sources & evidence

ORD record
ord-d7555fff07fa4be8a9a9725d57b3ab7b
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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