Sodium Bicarbonate → HCID 90320959, compound

HRID 2401257Notes

Reaction equation

HRID 2401257 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]([F:26])([F:25])[C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][N:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:13][CH:12]([CH3:14])[CH2:11][CH:8]([NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][NH:24][C:21]1[CH:20]=[N:19][C:18]([C:17]([F:26])([F:16])[F:25])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 546109tert-butyl N-(4-methyl-1-oxopentan-2-yl)carbamateHCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 90320959HCID 90320959, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The crude product of tert-butyl(4-methyl-1-oxopentan-2-yl)carbamate was dissolved in chloroform, 2-trifluoromethyl-5-aminopyridine (1.35 g) and sodium triacetoxyborohydride (3.52 g) were added thereto, and the mixture was stirred at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture, followed by extraction with chloroform and drying over anhydrous magnesium sulfate. The dissicant was filtered off, and then the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate) to afford tert-butyl (4-methyl-1-{[6-(trifluoromethyl)pyridin-3-yl]amino}pentan-2-yl)carbamate (2.58 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. filtrationThe dissicant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-eacffd8ab51f46f79b4d9c4705cd83eb
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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