Trifluoroacetic acid → HCID 68832534, compound

HRID 1787929Notes

Reaction equation

HRID 1787929 reaction equation
[C:1]([C:5]1[CH:29]=[CH:28][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[O:19])=[O:10])=[C:7]([O:30][CH:31]2[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(OC)C=CC=CC=1.[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53]>ClCCl>[F:55][C:54]([F:57])([F:56])[C:52]([OH:58])=[O:53].[C:1]([C:5]1[CH:29]=[CH:28][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[O:19])=[O:10])=[C:7]([O:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 68832569HCID 68832569, compound

Product 1

HCID 68832534HCID 68832534, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-3-carboxamide (0.099 g, 0.163 mmol) and anisole (0.1 mL) in dichloromethane (5 mL) was added TFA (0.5 mL). After 2 h, the solvent was removed in vacuo and the residue was suspended in toluene and concentrated in vacuo. The residue was then diluted with diethyl ether and concentrated in vacuo. Finally, the residue was again diluted with diethyl ether with vigorous stirring to yield a solid precipitate, which was filtered and washed with diethyl ether and dried in vacuum to give the title compound (0.089 g, 88%) as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. concentrationconcentrated in vacuo
  3. additionThe residue was then diluted with diethyl ether
  4. concentrationconcentrated in vacuo
  5. additionFinally, the residue was again diluted with diethyl ether
  6. customto yield a solid precipitate, which
  7. filtrationwas filtered
  8. washwashed with diethyl ether
  9. customdried in vacuum

Sources & evidence

ORD record
ord-3f80ed626d8348359710fe0cba5b3db1
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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