Trifluoroacetic acid → HCID 59285281, compound

HRID 906462Notes

Reaction equation

HRID 906462 reaction equation
FC(F)(F)C(O)=O.[Si]([O:15][CH2:16][C:17]([CH3:61])([CH3:60])[CH2:18][N:19]1[CH:28]=[C:27]([S:29]([CH:32]2[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]2)(=[O:31])=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:45]3[CH:50]=[C:49]([C:51](=[O:56])[NH:52][CH:53]4[CH2:55][CH2:54]4)[CH:48]=[C:47]([F:57])[C:46]=3[CH3:58])[CH:25]=2)[C:20]1=[O:59])(C(C)(C)C)(C)C>C(Cl)Cl>[CH:53]1([NH:52][C:51](=[O:56])[C:49]2[CH:50]=[C:45]([C:24]3[CH:25]=[C:26]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:59])[N:19]([CH2:18][C:17]([CH3:61])([CH3:60])[CH2:16][OH:15])[CH:28]=[C:27]4[S:29]([CH:32]3[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]3)(=[O:31])=[O:30])[C:46]([CH3:58])=[C:47]([F:57])[CH:48]=2)[CH2:54][CH2:55]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67135219HCID 67135219, compound

Product 1

HCID 59285281HCID 59285281, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic Acid (1 mL) was added to a solution of tert-butyl 4-({2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfonyl)piperidine-1-carboxylate (Example 60a, 0.116 g) in DCM (2 mL), and the reaction was stirred at room temperature for 30 min. The reaction was then azeotroped with toluene (3×10 mL), and the residue dissolved in methanol and purified by preparative HPLC (Phenomenex Gemini column using a 95-5% gradient of 0.2% aqueous NH3 in MeCN). Solvent removal and trituration with diethyl ether gave the title compound (0.026 g).

Workup

  1. customThe reaction was then azeotroped with toluene (3×10 mL)
  2. dissolutionthe residue dissolved in methanol
  3. custompurified by preparative HPLC (Phenomenex Gemini column
  4. customSolvent removal and trituration with diethyl ether

Sources & evidence

ORD record
ord-b6cab498ddc1466ca9117e076344339a
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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