Triethylamine → HCID 67479985, compound

HRID 509546Notes

Reaction equation

HRID 509546 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:23]#[CH:24])[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.[OH:25][N:26]=[C:27](Cl)[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1.CCN(CC)CC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:23]2[O:25][N:26]=[C:27]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[CH:24]=2)[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3303868HCID 3303868, compoundHCID 86667790HCID 86667790, compound

Product 1

HCID 67479985HCID 67479985, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-(5-bromo-3-ethynyl-2-pyridyl)-N-tert-butoxycarbonyl-carbamate (423 mg, 1.065 mmol) and N-hydroxy-4-methyl-benzimidoyl chloride (212.5 mg, 1.065 mmol) [Bioorganic & Medicinal Chemistry, 17(13), 4773-4785; 2009] in THF (10 mL) at ambient temperature was added Et3N (129.3 mg, 178.1 μL, 1.278 mmol) dropwise. The mixture was stirred at ambient temperature for 16 hours then at 65° C. for 2 hours. The mixture was concentrated in vacuo and the residue redissolved in DCM and washed with saturated aqueous NaHCO3 (×2) and brine (×1). The organic fraction was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 20% EtOAc/Petroleum Ether, loaded in DCM) to give the sub-title product as a white solid (472 mg, 84% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.28 (s, 18H), 2.39 (s, 3H), 7.39 (d, 2H), 7.60 (s, 1H), 7.68 (d, 2H), 8.73 (d, 1H) and 8.82 (d, 1H) ppm; MS (ES+) 532.0.

Workup

  1. waitat 65° C. for 2 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue redissolved in DCM
  4. washwashed with saturated aqueous NaHCO3 (×2) and brine (×1)
  5. dry with materialThe organic fraction was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 20% EtOAc/Petroleum Ether, loaded in DCM)

Sources & evidence

ORD record
ord-6905fc58054040cebf1cdefc650b368f
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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