Trifluoroacetic acid methylene chloride → HCID 58760537, compound

HRID 917036Notes

Reaction equation

HRID 917036 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-d967527ac7314d27bd2010f9b96c7aa5
Source dataset
uspto-grants-2007_09
Patent number
US07271178B2

Reaction notes

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