Trifluoroacetic acid → HCID 57602496, compound

HRID 1787911Notes

Reaction equation

HRID 1787911 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=2)=[O:27])=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:40]([C:38]1[CH:37]=[CH:36][C:16]([C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=2)=[O:27])=[O:18])=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:39]=1)([CH3:43])([CH3:41])[CH3:42]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57602477HCID 57602477, compound

Product 1

HCID 57602496HCID 57602496, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 3-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(tert-butyl)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-4-carboxamide (60 mg, 0.1 mmol) was mixed with anisole (1 mL) and CH2Cl2 (2 mL) then treated with trifluoroacetic acid (1 mL). The reaction was stirred at ambient temperature for 4 h, concentrated under vacuum to dryness and mixed with CH2Cl2. This was filtered through a 1 g SCX ion exchange column using 2 M NH3 in MeOH. Concentration to dryness gave 32 mg of the title compound as a solid.

Workup

  1. concentrationconcentrated under vacuum to dryness
  2. additionmixed with CH2Cl2
  3. filtrationThis was filtered through a 1 g SCX ion exchange column
  4. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-b8dcbc4583734b79ac012a5a7b4eaf05
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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