Hydrochloric Acid → HCID 87617685, compound

HRID 2111427Notes

Reaction equation

HRID 2111427 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[C:17]([NH2:18])=[CH:16][N:15]=[C:14]([Cl:19])[N:13]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>O1CCCC1>[NH2:18][C:17]1[C:12]([N:8]2[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]2)=[N:13][C:14]([Cl:19])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 87555139HCID 87555139, compound

Product 1

HCID 87617685HCID 87617685, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.114 g (0.0004 mole) of (rac)-1-(5-amino-2-chloro-pyrimidin-4-yl)-piperidine-3-carboxylic acid ethyl ester (V-67), 1 mL of tetrahydrofuran and 1 mL of 1M sodium hydroxide was stirred at ambient temperature for 3 hours. The mixture was acidified to pH=3 by the addition of 1M hydrochloric acid. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.0812 g of (rac)-1-(5-amino-2-chloro-pyrimidin-4-yl)-piperidine-3-carboxylic acid. This intermediate was stirred with 0.13 g (0.00034 mole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.058 g (0.00057 mol) of triethylamine and 2 mL of dichloromethane overnight at ambient temperature. The mixture was diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.075 g of (rac)-4-chloro-1,3,5,8-tetraaza-tricyclo[8.3.1.0*2,7*]tetradeca-2,4,6-trien-9-one (VI-67).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9af692c750c5498f8d73bf00e4f199df
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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