Trifluoroacetic acid → HCID 67280244, compound

HRID 1693307Notes

Reaction equation

HRID 1693307 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:13]2[CH2:12][S:11][N:10]=[C:9]([N:14](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:8]3=[N:29][N:30]([CH2:32][C:33]4[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([CH3:42])=[CH:35][N:34]=4)[N:31]=[C:6]([C:7]=23)[CH:5]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:14][C:9]1[C:8]2[C:7]3[C:6](=[N:31][N:30]([CH2:32][C:33]4[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([CH3:42])=[CH:35][N:34]=4)[N:29]=2)[CH:5]=[C:4]([CH2:3][CH2:2][OH:1])[C:13]=3[CH2:12][S:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86641344HCID 86641344, compound

Product 1

HCID 67280244HCID 67280244, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture composed of the above di-tert-butyl {8-(2-hydroxyethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate (16 mg), dichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) was stirred at room temperature for four hours. The reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate solution was placed into the resulting residue, followed by extraction with chloroform. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH silica gel chromatography (chloroform-methanol). The resulting oil was dissolved in dioxane, followed by lyophilization to obtain the title compound (8.3 mg, 78%) as an amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThen, the filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by NH silica gel chromatography (chloroform-methanol)
  7. dissolutionThe resulting oil was dissolved in dioxane

Sources & evidence

ORD record
ord-b78d6759f3e34c49b3fdbe3ee96593b3
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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