Trifluoroacetic acid → HCID 59285251, compound

HRID 906447Notes

Reaction equation

HRID 906447 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([F:45])[C:10]([CH3:44])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4[S:28]([N:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)(=[O:30])=[O:29])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[C:9]([F:45])[C:10]([CH3:44])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4[S:28]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)(=[O:30])=[O:29])[CH:12]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67390832HCID 67390832, compound

Product 1

HCID 59285251HCID 59285251, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-({6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfonyl)piperazine-1-carboxylate (Example 47c, 0.141 g) dissolved in DCM (10 mL) was added trifluoroacetic acid (0.5 mL). The reaction mixture was stirred at room temperature overnight. The reaction was purified by SCX, flushing with methanol (impurities), and eluting the product with 0.7 N methanolic ammonia. Purification by preparative HPLC (Xbridge column using a 95-5% gradient of aqueous ammonia in acetonitrile as eluent) followed by concentration under reduced pressure gave a white solid. This was combined with material from another reaction (scale: 0.097 g of starting material) to give the title compound (0.034 g) as a white solid.

Workup

  1. customThe reaction was purified by SCX
  2. customflushing with methanol (impurities)
  3. washeluting the product with 0.7 N methanolic ammonia
  4. customPurification by preparative HPLC (Xbridge column
  5. concentrationfollowed by concentration under reduced pressure
  6. customgave a white solid

Sources & evidence

ORD record
ord-a6965e985cc24181a3aa7fa7f781a313
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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