Dichloromethane → HCID 67280046, compound

HRID 1693315Notes

Reaction equation

HRID 1693315 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[C:20]2[CH2:19][S:18][N:17]=[C:16]([NH:21]C(=O)OC(C)(C)C)[C:15]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:13]([C:14]=23)[CH:12]=1.ClCCl>O1CCOCC1>[NH2:8][CH2:9][CH2:10][C:11]1[C:20]2[CH2:19][S:18][N:17]=[C:16]([NH2:21])[C:15]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:13]([C:14]=23)[CH:12]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86641347HCID 86641347, compound

Product 1

HCID 67280046HCID 67280046, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Trifluoroacetic acid (0.5 ml) was added to a mixture composed of the above tert-butyl {8-(2-aminoethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}carbamate (17 mg) and dichloromethane (2 ml), and then the mixture was stirred at room temperature for six hours. The solvent in the reaction mixture was evaporated, and a 0.2 N sodium hydroxide solution was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over sodium sulfate and filtered, and then the solvent in the filtrate was evaporated under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (chloroform-methanol) to obtain an oil. The oil was dissolved in dioxane (0.5 ml), followed by lyophilization to obtain the title compound (9.4 mg) as an amorphous.

Workup

  1. customThe solvent in the reaction mixture was evaporated
  2. additiona 0.2 N sodium hydroxide solution was added to the resulting residue
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe resulting residue was purified by NH silica gel column chromatography (chloroform-methanol)
  8. customto obtain an oil

Sources & evidence

ORD record
ord-a65fb982c601426da764565c136c251f
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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