Chloroform → HCID 67052313, compound

HRID 599412Notes

Reaction equation

HRID 599412 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([N:23]=[N:24][N:25]=2)[C:5]([CH3:22])=[C:6]([CH3:21])[C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[C:26](=O)(O)[O-].[Na+].[CH:31]([Cl:34])(Cl)Cl>>[Cl:34][CH2:31][C:26]1[N:8]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:7]2[C:6]([CH3:21])=[C:5]([CH3:22])[N:4]3[N:23]=[N:24][N:25]=[C:3]3[C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 67052289HCID 67052289, compound

Product 1

HCID 67052313HCID 67052313, compound

Procedure

Ethyl 2-chloroethanimidoate hydrochloride (ethyl chloroacetimidate hydrochloride) (2.58 g, 16.4 mmol) was added to a solution of tert-butyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butylcarbamate (3.80 g, 10.9 mmol) in chloroform (75 mL). The solution was stirred for 3 days, then saturated aqueous sodium bicarbonate (40 mL) was added. The aqueous phase was extracted with chloroform (3×40 mL). The organic phases were combined, washed with water (2×20 mL) and saturated aqueous sodium bicarbonate (20 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 4.3 g of tert-butyl 4-[8-(chloromethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butylcarbamate, which was used in the next step without purification.

Workup

  1. extractionThe aqueous phase was extracted with chloroform (3×40 mL)
  2. washwashed with water (2×20 mL) and saturated aqueous sodium bicarbonate (20 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1714d0b50f74beab90b576d6cb6db47
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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