Ammonia → HCID 66880346, compound

HRID 1893578Notes

Reaction equation

HRID 1893578 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])[C:7]1[CH:8]=[C:9]([C:14]2[S:15][CH:16]=[C:17]([C:19]([OH:21])=O)[N:18]=2)[CH:10]=[CH:11][C:12]=1[CH3:13])[CH3:2].[N:29]1C2C(=NC=CC=2)N(O)N=1.CCN=C=NCCCN(C)C.N>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:22][C:23]([O:24][CH2:25][CH3:26])=[O:27])[C:7]1[CH:8]=[C:9]([C:14]2[S:15][CH:16]=[C:17]([C:19]([NH2:29])=[O:21])[N:18]=2)[CH:10]=[CH:11][C:12]=1[CH3:13])[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 66880463HCID 66880463, compound

Product 1

HCID 66880346HCID 66880346, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (4.59 g, 11.3 mmol) of step A was dissolved in N,N-dimethylformamide (60 ml), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (1.97 g, 14.5 mmol) and WSC (2.80 g, 14.6 mmol) were added at room temperature, and the mixture was stirred at the same temperature for 70 min. Then, to the reaction mixture was added 28% aqueous ammonia (10 ml), and the mixture was further stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate and water, and the organic layer was extracted. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was washed with a diethyl ether-hexane=1:1 mixed solvent, and dried under reduced pressure to give the title compound (4.23 g, yield 92%) as a colorless solid.

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hr
  2. extractionthe organic layer was extracted
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. washThe obtained solid was washed with a diethyl ether-hexane=1:1 mixed solvent
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-0d5c62095e0f4c46bdbf147bf2997804
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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