4-Methylmorpholine → N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamide

HRID 1678446Notes

Reaction equation

HRID 1678446 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)[N:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH2:47][CH2:48][C:49]1[CH:56]=[CH:55][C:52]([C:53]#[N:54])=[CH:51][C:50]=1[C:57]([F:60])([F:59])[F:58]>ClCCl>[C:53]([C:52]1[CH:55]=[CH:56][C:49]([CH2:48][NH:47][C:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:4]3[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH:8][CH3:9])[N:5]=3)[CH2:15][CH2:14]2)=[O:18])=[C:50]([C:57]([F:58])([F:60])[F:59])[CH:51]=1)#[N:54]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 594477131-[4-Methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acidHCID 673396874-(Aminomethyl)-3-(trifluoromethyl)benzonitrile

Product 1

HCID 25261292N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamideYield 3.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (163 mg, 0.65 mmol) was dissolved in 10 mL of dichloromethane and treated with EDCI (150 mg, 0.72 mmol), HOBt (88 mg, 0.65 mmol), N-methylmorpholine (0.2 mL, 1.5 mmol), and 4-(aminomethyl)-3-(trifluoromethyl)benzonitrile (130 mg, 0.65 mmol) at room temperature for 12 hours. The reaction mixture was concentrated and purified by preparative HPLC to provide N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxamide (7 mg, 0.02 mmol, 2%) as a white solid. MS (ES+): m/e 434 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-295e61b002e2413595af4104f71f5cd3
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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