Boron Trichloride → HCID 178516588, compound

HRID 1433141Notes

Reaction equation

HRID 1433141 reaction equation
B(Cl)(Cl)Cl.C(OC([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:19]([C:23]3[CH:28]=[C:27]([Cl:29])[C:26]([O:30]CC4C=CC=CC=4)=[CH:25][C:24]=3[O:38]CC3C=CC=CC=3)=[N:20][NH:21][CH:22]=2)[CH2:14][CH2:13]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[NH3:12].[Cl:29][C:27]1[CH:28]=[C:23]([C:19]2[C:18]([N:15]3[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]3)=[CH:22][NH:21][N:20]=2)[C:24]([OH:38])=[CH:25][C:26]=1[OH:30]

Participants

6

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 178452255HCID 178452255, compound

Product 2

HCID 222AmmoniaHCID 178516588HCID 178516588, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride (1M solution in dichloromethane; 8 ml, 8 mmol) was added dropwise to a solution of 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (1.5 g, 2.6 mmol) in dichloromethane (15 ml) at 0° C. The resulting mixture was stirred at room temperature for 1 h, then basified with saturated sodium bicarbonate solution. The suspension was concentrated in vacuo, azeotroping with toluene until the residue was dry. The residue was triturated with dichloromethane:ethanol (1:1; 15 ml) and filtered. The filtrate was purified on a bond elute cartridge (20 g) eluting with dichloromethane:ethanol:ammonia, 50:8:1 then 20:8:1 to give 4-chloro-6-(4-piperazin-1-yl-1H-pyrazol-3-yl)-benzene-1,3-diol as a pale yellow solid (400 mg) (Example 2)

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. customazeotroping with toluene until the residue
  3. customwas dry
  4. customThe residue was triturated with dichloromethane:ethanol (1:1; 15 ml)
  5. filtrationfiltered
  6. customThe filtrate was purified on a bond
  7. washelute cartridge (20 g)
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-4a40e1a7253046bc876dec821b251f1c
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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