Isopropanol → HCID 21913456, compound

HRID 1008087Notes

Reaction equation

HRID 1008087 reaction equation
Cl[N:2]1[N:29]=[C:5]2[C:6]([N+:26]([O-])=O)=[C:7]([NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:8]([CH3:11])=[C:9]([CH3:10])[N:4]2[NH:3]1.CC(O)C>C1(C)C=CC=CC=1>[NH2:26][C:6]1[C:5]2[N:4]([N:3]=[N:2][N:29]=2)[C:9]([CH3:10])=[C:8]([CH3:11])[C:7]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 178428099HCID 178428099, compound

Product 1

HCID 21913456HCID 21913456, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen purge, 5% platinum on carbon (2.5 g) was added to a Parr vessel containing a solution of tert-butyl 2-{2-[(2-chloro-5,6-dimethyl-8-nitrotetrazolo[1,5-a]pyridin-7-yl)amino]ethoxy}ethylcarbamate (25.0 g, 63.2 mmol) in toluene (500 mL). The vessel was placed under hydrogen pressure (30 psi, 2.0×105 Pa) for four hours, and then 2-propanol (50 mL) was added. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with 2-propanol (500 mL) and ethanol (500 mL). The filtrate was concentrated under reduced pressure to yield 22.9 g of tert-butyl 2-{2-[(8-amino-5,6-dimethyltetrazolo[1,5-a]pyridin-7-yl)amino]ethoxy}ethylcarbamate as a brown oil.

Workup

  1. customUnder a nitrogen purge
  2. addition5% platinum on carbon (2.5 g) was added to a Parr vessel
  3. customfor four hours
  4. filtrationThe reaction mixture was filtered through a layer of CELITE
  5. filtrationfilter aid
  6. washthe filter cake was washed with 2-propanol (500 mL) and ethanol (500 mL)
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-694ee604abf84f50ac3b632cdd9fe5eb
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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