6-(6-benzyloxypyrid-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide → HCID 178521924, compound

HRID 2363718Notes

Reaction equation

HRID 2363718 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([CH:21]=[C:22]([C:24]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:25])[N:23]=3)[CH:20]=2)[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O>[OH:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([CH:21]=[C:22]([C:24]([NH:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:25])[N:23]=3)[CH:20]=2)[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 687800626-(6-benzyloxypyrid-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Product 1

HCID 178521924HCID 178521924, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 300 mg of 6-(6-benzyloxypyrid-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in 3 mL of trifluoroacetic acid is stirred at 25° C. for 48 hours and then evaporated to dryness under reduced pressure at 45° C. The residue is triturated with ether, filtered off and dried, and then triturated again with 2 mL of saturated sodium bicarbonate solution, washed twice with 2 mL of water and twice with 2 mL of ethyl ether and dried under reduced pressure to give 168 mg of 6-(6-hydroxypyrid-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid.

Workup

  1. customevaporated to dryness under reduced pressure at 45° C
  2. customThe residue is triturated with ether
  3. filtrationfiltered off
  4. customdried
  5. customtriturated again with 2 mL of saturated sodium bicarbonate solution
  6. washwashed twice with 2 mL of water and twice with 2 mL of ethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-066bcb2deac843cc9ebe56b00743d5df
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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