Trifluoroacetic acid methylene chloride → HCID 58760537, compound

HRID 1788253Notes

Reaction equation

HRID 1788253 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[N:14]2[CH:15]=[C:16]([C:29](=[O:36])[NH:30][O:31][CH2:32][CH:33]3[CH2:35][CH2:34]3)[C:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[Cl:28])=[C:18]([Cl:19])[C:13]2=[N:12][CH:11]=1)C)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>>[CH:33]1([CH2:32][O:31][NH:30][C:29]([C:16]2[C:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[Cl:28])=[C:18]([Cl:19])[C:13]3[N:14]([C:10]([CH2:9][NH:7][CH3:6])=[CH:11][N:12]=3)[CH:15]=2)=[O:36])[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86596994HCID 86596994, compound

Product 1

HCID 58760537HCID 58760537, compoundYield 83%

Procedure

A solution of [7-(4-bromo-2-chlorophenylamino)-8-chloro-6-cyclopropylmethoxy-carbamoyl-imidazo[1,2-a]pyridin-3-ylmethyl]-methyl-carbamic acid tert-butyl ester (62) in 1:1 dichloromethane/trifluoroacetic acid was stirred for two hours. Solvent was removed under reduced pressure and the residue redissolved into ethyl acetate. The organic solution was washed with saturated aqueous potassium carbonate and brine. The aqueous washes were back-extracted with ethyl acetate. The combined organic extracts are dried over NaSO4, filtered, and concentrated in vacuo to provide the desired product as a yellow solid (8 mg, 83%). MS (APCI+) m/z 512, 514, 516 (M+; Cl, Br pattern) detected. 1H NMR (400 MHz, methanol-d4) δ 8.72 (s, 1H), 7.58 (s, 1H), 7.54 (s, 1H), 7.25 (d, 1H), 6.55 (d, 1H), 4.23 (s, 2H), 3.67 (d, 2H), 2.51 (s, 3H), 1.13 (m, 1H), 0.50 (d, 2H), 0.24 (d, 2H).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue redissolved into ethyl acetate
  3. washThe organic solution was washed with saturated aqueous potassium carbonate and brine
  4. extractionThe aqueous washes were back-extracted with ethyl acetate
  5. dry with materialThe combined organic extracts are dried over NaSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c93b4d4fd2a452f83f81f842a2239f5
Source dataset
uspto-grants-2009_03
Patent number
US07511058B2

Reaction notes

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