Methylamine → HCID 86641328, compound

HRID 1693294Notes

Reaction equation

HRID 1693294 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].[Cl:55]C(Cl)C.[CH3:59][NH2:60].[OH-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[ClH:55].[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][CH:31]([NH:60][CH3:59])[C:32]4[CH2:33][S:34][N:35]=[C:36]([NH2:37])[C:27]([C:28]=43)=[N:26]2)[C:18]=1[CH3:54]

Participants

9

Reactant 5

HCID 6329MethylamineHCID 63651,1-DichloroethaneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 67279997HCID 67279997, compound

Product 1

HCID 86641328HCID 86641328, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

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 (28 mg), dichloroethane (0.5 mL), a 2 N solution of methylamine in tetrahydrofuran (0.1 mL) and acetic acid (6 μL), and the mixture was stirred at room temperature for 17 hours. Methanol (three drops) was added dropwise to the reaction mixture, and then a 0.2 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. A 4 N solution of hydrochloric acid in dioxane (20 μL) was added to the resulting solid. Methanol and diethyl ether were added and the precipitated solid was collected by filtration to obtain the title compound (5.7 g, 28%) as a solid.

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. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe resulting residue was purified by reversed phase liquid chromatography
  8. additionA 4 N solution of hydrochloric acid in dioxane (20 μL) was added to the resulting solid
  9. additionMethanol and diethyl ether were added
  10. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-017cd40202c440d88307f1c9283c19e8
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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