O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 67957366, compound

HRID 1189627Notes

Reaction equation

HRID 1189627 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].[NH2:11][C:12]1[C:13]([Cl:21])=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15][NH2:16].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[NH2:11][C:12]1[C:13]([Cl:21])=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15][NH:16][C:4](=[O:5])[C:3]([CH3:8])([C:2]([F:10])([F:9])[F:1])[CH3:7]

Participants

4

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 198673673,3,3-Trifluoro-2,2-dimethylpropanoic acidHCID 568399683-(Aminomethyl)-2,6-dichloroaniline

Product 1

HCID 67957366HCID 67957366, compound

Conditions

Temperature
45 °C

Procedure

A mixture of 2-trifluoromethyl-isobutyric acid (2.85 mg, 18 mmol), 3-amino-2,4-dichloro-benzylamine (3.49 g, 18 mmol), TBTU (5.98 g, 19 mmol), TEA (7.7 mL, 55 mmol) and 65 mLTHF is stirred at 45° C. overnight. The mixture is washed with sat aq NaHCO3-solution and water and the organic phase is dried with Na2SO4, filtered, concentrated and purified by chromatography (silicagel, Cyclohexane:EtOAc 11:1→7:3).

Workup

  1. washThe mixture is washed with sat aq NaHCO3-solution and water
  2. dry with materialthe organic phase is dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by chromatography (silicagel, Cyclohexane:EtOAc 11:1→7:3)

Sources & evidence

ORD record
ord-ec7ddb427cb846f4be638c7cb72e6512
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

Loading…