O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 59332716, compound

HRID 387296Notes

Reaction equation

HRID 387296 reaction equation
N.CO.[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([C:14](O)=[O:15])[CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][S:20](=[O:25])(=[O:24])[CH2:19]1.C[N:27](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([C:14]([NH2:27])=[O:15])[CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][S:20](=[O:25])(=[O:24])[CH2:19]1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21705897Ammonia methanolHCID 59332773HCID 59332773, compound

Product 1

HCID 59332716HCID 59332716, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of NH3/MeOH (40 mL) was added to a mixture of 5-bromo-3-((1,1-dioxo-tetrahydro-2H-thiopyran-3-yl)methyl)-1H-indole-7-carboxylic acid (1.30 g, 0.0034 mol), TEA (0.68 g, 0.0067 mol), and TBTU (2.16 g, 0.067 mol) in DCM (30 mL). The resulting mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was washed with water and extracted with DCM (2×100 mL). The organic layers were dried, filtered, concentrated under reduced pressure, and purified by chromatography eluting with a mixture of DCM:MeOH (60:1), giving 0.94 g (72.5%) of the title compound.

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. extractionextracted with DCM (2×100 mL)
  4. customThe organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by chromatography
  8. washeluting with a mixture of DCM:MeOH (60:1)

Sources & evidence

ORD record
ord-f90efbb452c345c781adf5ff3f5efd2b
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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