1-Methylpiperazine → HCID 59543590, compound

HRID 1697662Notes

Reaction equation

HRID 1697662 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[C:17]([C:19]1([NH:22][C:23]([C@@H:25]2[CH2:29][C@@H:28]([S:30]([C:33]3[CH:38]=[CH:37][C:36](F)=[CH:35][C:34]=3[C:40]([F:43])([F:42])[F:41])(=[O:32])=[O:31])[CH2:27][N:26]2[C:44]2[N:45]([CH:50]3[CH2:53][CH2:52][CH2:51]3)[N:46]=[C:47]([CH3:49])[CH:48]=2)=[O:24])[CH2:21][CH2:20]1)#[N:18]>C(#N)C>[C:17]([C:19]1([NH:22][C:23]([C@@H:25]2[CH2:29][C@@H:28]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:35][C:34]=3[C:40]([F:43])([F:42])[F:41])(=[O:32])=[O:31])[CH2:27][N:26]2[C:44]2[N:45]([CH:50]3[CH2:53][CH2:52][CH2:51]3)[N:46]=[C:47]([CH3:49])[CH:48]=2)=[O:24])[CH2:21][CH2:20]1)#[N:18]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 66770568HCID 66770568, compound

Product 1

HCID 59543590HCID 59543590, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methylpiperazine (10 ul, 116 umol; CAS Reg. No. 109-01-3) and DIEA (20 ul, 93 umol) were added to a solution of (2S,4R)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide (25 mg, 46 umol; example 388 g) in acetonitrile (400 ul) under an argon atmosphere. The reaction mixture was stirred at ambient temperature for 72 h, the solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give the title compound (14 mg, 23 umol; 49%) as colorless oil. MS (ESI): m/z=618.2 [M−H]−.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ceda0028bf2446f3af71c7f1d07f704f
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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