Boron trifluoride etherate → HCID 53443879, compound

HRID 1518281Notes

Reaction equation

HRID 1518281 reaction equation
[N:1]1C=NC=N[CH:2]=1.[NH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[N:11]=[CH:10][C:9]=1[C:20](O)=O.B(F)(F)F.CCOCC>CS(C)=O.CCOC(C)=O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:8]3=[N:7][CH:2]=[N:1][CH:20]=[C:9]3[CH:10]=[N:11]2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 92621,3,5-TriazineHCID 40570295-Amino-1-(4-bromophenyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 53443879HCID 53443879, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1,3,5-triazine (0.575 g, 7.09 mmol) and compound 21A (2 g, 7.09 mmol) in DMSO (30 mL) was added boron trifluoride etherate (1.078 mL, 8.51 mmol). The resulting mixture was heated at 120° C. for 20 h, cooled, diluted with EtOAc and washed with 1% NaOH and brine. The organic layer was dried over Na2SO4 and concentrated. The residue was triturated with small amount of EtOAc and the precipitate was collected to provide the desired product: 1H NMR (400 MHz, DMSO-D6) δ ppm 9.47 (1H, s), 9.16 (1H, s), 8.68 (1H, s), 8.22 (2H, d), 7.80 (2H, d).

Workup

  1. temperaturecooled
  2. washwashed with 1% NaOH and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was triturated with small amount of EtOAc
  6. customthe precipitate was collected

Sources & evidence

ORD record
ord-d52a7a17ca0a4f60a515ac87e9d2b097
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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