Triethylamine → HCID 68778603, compound

HRID 2264444Notes

Reaction equation

HRID 2264444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([C:18]([F:21])([F:20])[F:19])=[N:13][C:14](Cl)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>CC(N(C)C)=O.C(#N)C>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([NH:35][C:14]2[N:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[C:11]([C:9](=[O:10])[NH:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:16][N:15]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 2780363HCID 2780363, compound

Product 1

HCID 68778603HCID 68778603, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid (4-chloro-phenyl)-amide (0.8 g, 2.38 mmol, 1.0 equiv; commercially available from Maybridge, UK), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.72 g, 3.57 mmol, 1.5 equiv; commercially available) and triethylamine (0.49 mL, 0.36 g, 3.57 mmol, 1.5 equiv) in anhydrous DMAc (2 mL) and acetonitrile (9 mL) was heated by microwave irradiation to 120° C. for 20 min. The organic phase was concentrated under reduced pressure and the crude material purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 1.0 g (84%) of the title compound. MS (ISP): 500.3 [M+H]+.

Workup

  1. concentrationThe organic phase was concentrated under reduced pressure
  2. customthe crude material purified by silica column chromatography
  3. washeluting with a gradient of heptane/ethyl acetate providing 1.0 g (84%) of the title compound

Sources & evidence

ORD record
ord-935f96bb3e9e41679d129a1594809018
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

Loading…