Diisopropylamine → Rac-cis-(2-(((5-chloropyrimidin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(2-(trifluoromethoxy)phenyl)methanone

HRID 60879

Reaction equation

HRID 60879 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][C@H:10]2[C@@H:15]([CH3:16])[CH2:14][CH2:13][CH2:12][NH:11]2)=[N:6][CH:7]=1.C(NC(C)C)(C)C.[F:24][C:25]([F:37])([F:36])[O:26][C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][C@H:10]2[C@@H:15]([CH3:16])[CH2:14][CH2:13][CH2:12][N:11]2[C:29]([C:28]2[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=2[O:26][C:25]([F:24])([F:36])[F:37])=[O:30])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 27772412-(Trifluoromethoxy)benzoyl ChlorideHCID 131737160rac-cis-5-chloro-N-((3-methylpiperidin-2-yl)methyl)pyrimidin-2-amine

Product 1

HCID 131737159Rac-cis-(2-(((5-chloropyrimidin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(2-(trifluoromethoxy)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the forementioned rac-cis-5-chloro-N-((3-methylpiperidin-2-yl)methyl)pyrimidin-2-amine and diisopropylamine (3 eq) in DCM was added 2-(trifluoromethoxy)benzoyl chloride (1.2 eq) dropwise. The reaction was stirred at reflux for 3 h and concentrated in vacuo. The crude reaction mixture was purified by reverse-phase preparative HPLC to afford the title compound. (ESI) 429.1 (M+H).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe crude reaction mixture
  4. customwas purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-eaaf1ad515e04aa992625b49ead578e7
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Linked notes

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