Sodium Hydroxide → HCID 67225632, compound

HRID 624359Notes

Reaction equation

HRID 624359 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=O)[CH3:15])=[CH:4][CH:3]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[BH3-]C#N.[Na+].[OH-].[Na+]>ClCCl.CO.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)[CH3:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 201001921-(4'-Chloro[1,1'-biphenyl]-2-yl)ethan-1-one

Product 1

HCID 67225632HCID 67225632, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of EXAMPLE 110A (1.9 g) in dichloromethane (3 mL) was treated with 1M titanium(IV) chloride in dichloromethane (9.06 mL), cooled to 0° C., treated with tert-butyl piperazine-1-carboxylate (3.07 g), stirred at ambient temperature for 3 hours, treated with NaCNBH3 (0.828 g) in methanol (5 ml), stirred at room temperature overnight, neutralized with aqueous NaOH and concentrated. The concentrate was treated with ethyl acetate and filtered. The organic filtrate was washed with water and concentrated. The concentrate was dissolved in methanol/trifluoroacetic acid/dimethylsulfoxide, loaded onto a reverse phase C18 column and eluted with 0-80% acetonitrile in 0.1% trifluoroacetic acid water over 70 minutes.

Workup

  1. stirringstirred at room temperature overnight
  2. concentrationconcentrated
  3. additionThe concentrate was treated with ethyl acetate
  4. filtrationfiltered
  5. washThe organic filtrate was washed with water
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in methanol/trifluoroacetic acid/dimethylsulfoxide
  8. washeluted with 0-80% acetonitrile in 0.1% trifluoroacetic acid water over 70 minutes

Sources & evidence

ORD record
ord-4986bc2eb0e246adaf1c59c896b163bf
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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