Trifluoroacetic acid → HCID 59398030, compound

HRID 2193369Notes

Reaction equation

HRID 2193369 reaction equation
C(OC(=O)[N:7]([CH2:29][C:30]1[C:31]([Cl:42])=[CH:32][C:33]2[S:34][CH2:35][C:36](=[O:41])[N:37]([CH3:40])[C:38]=2[N:39]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]2=[O:28])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[Cl:42][C:31]1[C:30]([CH2:29][NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[N:19]=[CH:18][C:17]3=[O:28])[CH2:10][CH2:9]2)=[N:39][C:38]2[N:37]([CH3:40])[C:36](=[O:41])[CH2:35][S:34][C:33]=2[CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398291HCID 59398291, compound

Product 1

HCID 59398030HCID 59398030, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 20 mL of a chloroform solution containing 0.23 g of tert-butyl(7-chloro-4-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-ylmethyl)(1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 20 mL of trifluoroacetic acid was added and stirred at room temperature for 12 hours. After solvents of the reaction mixture were removed under reduced pressure and the residue was alkalized by aqueous saturated sodium hydrogen carbonate solution, it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1], to give 0.16 g of 1-(2-(4-((7-chloro-4-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a pale brown foam.

Workup

  1. additionwas added
  2. customAfter solvents of the reaction mixture were removed under reduced pressure
  3. extractionwas extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-4ba96d3670f241f0b6372ef1e27146be
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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