1-Methylpiperazine → HCID 178488054, compound

HRID 77108Notes

Reaction equation

HRID 77108 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][CH:11]([C:14](O)=[O:15])[CH2:10]2)=[CH:5][C:4]=1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:19]=2[N:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52][N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.C([O-])(O)=O.[Na+]>ClCCl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][CH:11]([C:14]([N:56]3[CH2:57][CH2:58][N:53]([CH3:52])[CH2:54][CH2:55]3)=[O:15])[CH2:10]2)=[CH:5][C:4]=1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:19]=2[N:18]=1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178488055HCID 178488055, compound

Product 1

HCID 178488054HCID 178488054, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

Method P—Step a To a vial with 1-[4-Chloro-3-(5-methoxy-1H-benzoimidazol-2-yl)-phenyl]-pyrrolidine-3-carboxylic acid hydrochloride (obtained as described in general method 3,4, step e) (0.10 g, 0.25 mmol), HATU (0.10 g, 0.26 mmol), TEA (0.07 mL, 0.53 mmol) and 1-methyl-piperazine (0.04 mL, 0.33 mmol), dichloromethane (2 mL) was added and the reaction mixture was heated at 35° C. overnight. Reaction was cooled to room temperature, saturated NaHCO3 solution (2 mL) was added with stirring, the organic layer recovered by filtration through phase separator, and the solvent removed under reduced pressure. The crude was purified by SCX, trituration from diethyl ether and finally by preparative HPLC to obtain 0.04 g of the title compound (34%).

Workup

  1. customReaction
  2. temperaturewas cooled to room temperature
  3. filtrationthe organic layer recovered by filtration through phase separator
  4. customthe solvent removed under reduced pressure
  5. customThe crude was purified by SCX, trituration from diethyl ether and finally by preparative HPLC

Sources & evidence

ORD record
ord-6ed64bcb8756418b9a7dda63e521a505
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

Loading…