Triethylamine → HCID 68779242, compound

HRID 2264462Notes

Reaction equation

HRID 2264462 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>CC(N(C)C)=O.C(#N)C>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:2]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]3[C:4](=[N:5][CH:6]=[CH:7][N:8]=3)[N:3]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 640835HCID 640835, compoundHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 68779242HCID 68779242, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-chloro-4-phenyl-pteridine (0.33 g, 1.36 mmol, 1.0 equiv; commercially available from Specs Research Laboratory, The Netherlands), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.41 g, 2.04 mmol, 1.5 equiv; commercially available) and triethylamine (0.28 mL, 0.21 g, 2.04 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 0.5 g (91%) of the title compound. MS (ISP): 407.4 [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 0.5 g (91%) of the title compound

Sources & evidence

ORD record
ord-169bfdd177764b29af7906c13d12e4ab
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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