1,1-Dichloroethane → HCID 86641332, compound

HRID 1693298Notes

Reaction equation

HRID 1693298 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][C:17]1[C:22]([CH3:23])=[CH:21][N:20]=[C:19]([CH2:24][N:25]2[N:53]=[C:29]3[CH2:30][C:31](=O)[C:32]4[CH2:33][S:34][N:35]=[C:36]([N:37](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:27]([C:28]=43)=[N:26]2)[C:18]=1[CH3:54].ClC(Cl)C.[CH:59]1([NH2:63])[CH2:62][CH2:61][CH2:60]1.[OH-].[Na+]>CO.C(O)(=O)C>[CH:59]1([NH:63][CH:31]2[C:32]3[CH2:33][S:34][N:35]=[C:36]([NH2:37])[C:27]4=[N:26][N:25]([CH2:24][C:19]5[C:18]([CH3:54])=[C:17]([O:16][CH3:15])[C:22]([CH3:23])=[CH:21][N:20]=5)[N:53]=[C:29]([C:28]=34)[CH2:30]2)[CH2:62][CH2:61][CH2:60]1

Participants

8

Reactant 5

HCID 63651,1-DichloroethaneHCID 14798Sodium HydroxideHCID 75645CyclobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67279997HCID 67279997, compound

Product 1

HCID 86641332HCID 86641332, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 176Acetic AcidSolvent

Procedure

Sodium triacetoxyborohydride (16 mg) was added to a mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 40 (34 mg), dichloroethane (0.7 ml), cyclobutylamine (15 μl) and acetic acid (10 μl), and the mixture was stirred at room temperature overnight. Methanol (three drops) was added dropwise to the reaction mixture, and then a 1 N sodium hydroxide solution was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. Dichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue, and the mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by reversed phase liquid chromatography. The resulting oil was dissolved in dioxane, followed by lyophilization to obtain the title compound (6.3 mg, 25%) as a colorless amorphous.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionDichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue
  6. stirringthe mixture was stirred at room temperature for two hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe resulting residue was purified by reversed phase liquid chromatography
  9. dissolutionThe resulting oil was dissolved in dioxane

Sources & evidence

ORD record
ord-1cc467a012ac41e9b4c9b54a0124b5cf
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

Loading…