Triethylamine hydrochloride → HCID 178492267, compound

HRID 1693283Notes

Reaction equation

HRID 1693283 reaction equation
[C:1]([CH:3]1[C:12]2[CH2:11][CH2:10][C:9]3=[N:13][N:14]([CH2:16][C:17]4[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=4)[N:15]=[C:7]([C:8]=23)[C:6]([N:27](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:5][S:4]1)#[N:2].Cl.C(N(CC)CC)C.[N-:50]=[N+:51]=[N-:52].[Na+]>CN(C)C=O>[CH3:25][O:24][C:21]1[C:20]([CH3:26])=[CH:19][N:18]=[C:17]([CH2:16][N:14]2[N:13]=[C:9]3[CH2:10][CH2:11][C:12]4[CH:3]([C:1]5[NH:2][N:52]=[N:51][N:50]=5)[S:4][N:5]=[C:6]([NH2:27])[C:7]([C:8]=43)=[N:15]2)[C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 86641322HCID 86641322, compound

Product 1

HCID 178492267HCID 178492267, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture composed of di-tert-butyl {7-cyano-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Step 4) of Example 23 (53 mg), N,N-dimethylformamide (1 mL), triethylamine hydrochloride (14.5 m) and sodium azide (6.8 mg) was sealed in a tube and heated with stirring at a bath temperature of 105° C. for 15 hours. After cooling to room temperature, the reaction solution was separated with ethyl acetate and a 0.1 N sodium hydroxide solution. The aqueous layer was made acidic with a 0.1 N hydrochloric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Dichloromethane (2 mL) and trifluoroacetic acid (0.5 mL) were added to the resulting residue, and the mixture was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol-lower layer of water) to obtain the title compound (5.6 mg, 19%) as a solid.

Workup

  1. customwas sealed in a tube
  2. temperatureheated
  3. temperatureAfter cooling to room temperature
  4. customthe reaction solution was separated with ethyl acetate
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. additionDichloromethane (2 mL) and trifluoroacetic acid (0.5 mL) were added to the resulting residue
  11. stirringthe mixture was stirred at room temperature for two hours
  12. concentrationThe reaction solution was concentrated under reduced pressure
  13. customthe resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol-lower layer of water)

Sources & evidence

ORD record
ord-98974c351713422a8d1d859108c41198
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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