Triethylamine → HCID 86615295, compound

HRID 2264446Notes

Reaction equation

HRID 2264446 reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:14]([C:20]([F:23])([F:22])[F:21])=[N:15][C:16](Cl)=[N:17][CH:18]=2)=[O:12])=[CH:6][CH:5]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C(N(CC)CC)C>CC(N(C)C)=O.C(#N)C>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH:39][C:16]2[N:15]=[C:14]([C:20]([F:23])([F:22])[F:21])[C:13]([C:11](=[O:12])[NH:10][C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:25])([F:24])[F:1])=[CH:5][CH:6]=3)=[CH:18][N:17]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 2780276HCID 2780276, compound

Product 1

HCID 86615295HCID 86615295, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid (4-trifluoromethoxy-phenyl)-amide (0.8 g, 2.07 mmol, 1.0 equiv; commercially available from Maybridge, UK), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.62 g, 3.11 mmol, 1.5 equiv; commercially available) and triethylamine (0.43 mL, 0.32 g, 3.11 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 0.92 g (81%) of the title compound. MS (ISP): 550.2 [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 0.92 g (81%) of the title compound

Sources & evidence

ORD record
ord-6bab16a98c544e56b9e6432c64a0d643
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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