Acetonitrile → HCID 67400646, compound

HRID 913103Notes

Reaction equation

HRID 913103 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8](Cl)=[CH:7]N=1)=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[C:26](#N)[CH3:27].[CH2:29](N(C(C)C)C(C)C)[CH3:30]>>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:10]2[C:5]3[C:3](=[CH:29][CH:30]=[CH:26][CH:27]=3)[CH:7]=[CH:8][N:9]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 67400646HCID 67400646, compound

Procedure

A solution of 5-chloro-pyrazine-2-carboxylic acid methyl ester (1.33 g, 7.68 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (2.00 g, 10.00 mmol, 1.3 equiv; commercially available) in N-ethyl diisopropylamine (12 mL) and acetonitrile (16 mL) was heated by microwave irradiation to 160° C. for 40 min. The solvent was evaporated under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 1.62 g (63%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.27-1.41 (m, 2H), 1.41 (s, 9H), 1.86-1.90 (m, 2H), 2.88-2.97 (m, 2H), 3.79 (s, 3H), 3.85-3.91 (m, 2H), 3.96-4.03 (m, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.95 (s, 1H), 8.58 (s, 1H). MS (ISP): 337.5 [M+H]+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue purified by silica column chromatography
  3. washeluting with a gradient of heptane/ethyl acetate providing 1.62 g (63%) of the title compound

Sources & evidence

ORD record
ord-ecc5647a5e7d463395ce74b7ff2a2d32
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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