Trifluoroacetic acid → HCID 22485111, compound

HRID 2181055Notes

Reaction equation

HRID 2181055 reaction equation
C(O[C:6]([N:8]([C:11]1[CH:38]=[CH:37][C:14]([CH2:15][N:16]2[C:20]3=[N:21][C:22]([C:25](=[O:35])[NH:26][S:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=[O:29])=[O:28])=[CH:23][CH:24]=[C:19]3[N:18]=[C:17]2[CH3:36])=[C:13]([Cl:39])[CH:12]=1)CC)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:39][C:13]1[CH:12]=[C:11]([NH:8][CH3:6])[CH:38]=[CH:37][C:14]=1[CH2:15][N:16]1[C:20]2=[N:21][C:22]([C:25](=[O:35])[NH:26][S:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=[O:29])=[O:28])=[CH:23][CH:24]=[C:19]2[N:18]=[C:17]1[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22485002HCID 22485002, compound

Product 1

HCID 22485111HCID 22485111, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-(N-(tert-butoxycarbonyl)-N-ethylamino)-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-8cebc7b76d9a416583cea36130b93e6d
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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