Triethylamine → HCID 71208520, compound

HRID 1622257Notes

Reaction equation

HRID 1622257 reaction equation
[OH:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[O:29][C:14]3=[CH:15][N:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[CH2:12]2)[CH2:7][CH2:6]1)=[NH:4].[C:30](Cl)(=O)[CH:31]([CH3:33])[CH3:32].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH:31]([C:33]1[O:1][N:2]=[C:3]([N:5]2[CH2:6][CH2:7][CH:8]([CH:11]3[O:29][C:14]4=[CH:15][N:16]=[C:17]([C:19]5[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=5)[CH:18]=[C:13]4[CH2:12]3)[CH2:9][CH2:10]2)[N:4]=1)([CH3:32])[CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 178504662HCID 178504662, compound

Product 1

HCID 71208520HCID 71208520, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-hydroxy-4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxamidine (45 mg), isobutyryl chloride (12 μL), and triethylamine (50 μL) in tetrahydrofuran (5 mL) is stirred for 30 min at room temperature prior to heating to 80° C. for 5 h. The heating is continued over night at reflux. The reaction mixture is diluted with ethyl acetate after cooling to room temperature, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is triturated with a small amount of methanol and the precipitate is filtered off, washed with diethyl ether, and dried to give the title compound. LC (method 5): tR=1.30 min; Mass spectrum (ESI+): m/z=469 [M+H]+.

Workup

  1. temperatureto heating to 80° C. for 5 h
  2. waitThe heating is continued over night
  3. temperatureat reflux
  4. temperatureafter cooling to room temperature
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue is triturated with a small amount of methanol
  9. filtrationthe precipitate is filtered off
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-bf05d6ff10cb45d0a769c7a76bd9697e
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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