O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 52919085, compound

HRID 1846080Notes

Reaction equation

HRID 1846080 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])=[O:36])=[CH:29][C:25]=1[C:26]([OH:28])=O.[Br:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:58])[C:50]2[CH:55]=[C:54]([NH2:56])[CH:53]=[CH:52][C:51]=2[Cl:57])=[CH:44][CH:43]=1>C1COCC1>[Cl:57][C:51]1[CH:52]=[CH:53][C:54]([NH:56][C:26](=[O:28])[C:25]2[CH:29]=[C:30]([CH2:33][NH:34][C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])=[O:36])[CH:31]=[CH:32][C:24]=2[Cl:23])=[CH:55][C:50]=1[C:49]([NH:48][C:45]1[CH:46]=[CH:47][C:42]([Br:41])=[CH:43][CH:44]=1)=[O:58]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16784957HCID 16784957, compoundHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid

Product 1

HCID 52919085HCID 52919085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of TBTU (108 mg, 0.338 mmol), TEA (0.128 mL), 2-chloro-5-(tert-butylcarbonylamino)methyl-benzoic acid (83 mg, 0.31 mmol) and 5 mL THF was stirred for 15 min at rt. Then N-(4-bromophenyl)-2-chloro-5-amino-benzoic acid amide (100 mg, 0.31 mmol, prepared analogously to 2d/2e) was added and it was stirred for 3 h at rt and for additional 3 h at reflux. The mixture was concentrated i.vac., EtOAc was added and the organic phase was washed with 1M NaOH, water, 2M aq. HCl-solution, water and brine and dried with Na2SO4. The crude mixture was concentrated i.vac. and purified by chromatography (silica gel, petrol ether/EtOAc 60/40→55/45) to furnish the title compound.

Workup

  1. additionwas added
  2. stirringit was stirred for 3 h at rt and for additional 3 h
  3. temperatureat reflux
  4. concentrationThe mixture was concentrated i.vac
  5. addition, EtOAc was added
  6. washthe organic phase was washed with 1M NaOH, water, 2M aq. HCl-solution, water and brine
  7. dry with materialdried with Na2SO4
  8. concentrationThe crude mixture was concentrated i.vac
  9. customand purified by chromatography (silica gel, petrol ether/EtOAc 60/40→55/45)

Sources & evidence

ORD record
ord-eb196e17f3ba4b35a67428cfc4f4638e
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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