Trifluoroacetic acid → HCID 22485111, compound

HRID 1368263Notes

Reaction equation

HRID 1368263 reaction equation
C(O[C:6]([N:8]([C:10]1[CH:37]=[CH:36][C:13]([CH2:14][N:15]2[C:19]3=[N:20][C:21]([C:24](=[O:34])[NH:25][S:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:28])=[O:27])=[CH:22][CH:23]=[C:18]3[N:17]=[C:16]2[CH3:35])=[C:12]([Cl:38])[CH:11]=1)C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:38][C:12]1[CH:11]=[C:10]([NH:8][CH3:6])[CH:37]=[CH:36][C:13]=1[CH2:14][N:15]1[C:19]2=[N:20][C:21]([C:24](=[O:34])[NH:25][S:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:28])=[O:27])=[CH:22][CH:23]=[C:18]2[N:17]=[C:16]1[CH3:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22484977HCID 22484977, compound

Product 1

HCID 22485111HCID 22485111, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-(N-(tert-butoxycarbonyl)-N-methylamino)-2-chlorobenzyl)-2-methyl-5-(1-pentanesulfonylcarbamoyl)-3H-imidazo[4,5-b]pyridine (1.91 g) in dichloromethane (19 ml) was added trifluoroacetic acid (14.5 ml) under ice-cooling, and the mixture was stirred for 1 hr. The solvent was evaporated and methanol (19 ml) was added to the residue for re-dissolution. Water (9.5 ml) was added and 1N aqueous sodium hydroxide solution was added dropwise under ice-cooling to adjust to about pH 4. The resulting precipitate was collected by filtration and dried under reduced pressure to give 3-(2-chloro-4-(methylamino)benzyl)-2-methyl-5-(1-pentanesulfonylcarbamoyl)-3H-imidazo[4,5-b]pyridine (1.53 g) as a white powder.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. additionmethanol (19 ml) was added to the residue for re-dissolution
  4. additionWater (9.5 ml) was added
  5. addition1N aqueous sodium hydroxide solution was added dropwise under ice-
  6. temperaturecooling
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-87247ea4945847d0aa626e7e92d32d0d
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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