Diisopropylethylamine → HCID 86704557, compound

HRID 633473Notes

Reaction equation

HRID 633473 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[NH:14][N:13]=[N:12]1.Cl.[OH:18][CH:19]1[CH2:22][NH:21][CH2:20]1.[CH3:23]CN(C(C)C)C(C)C>CC#N>[OH:18][CH:19]1[CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[N:11]2[C:15](=[O:16])[N:14]([CH3:23])[N:13]=[N:12]2)[CH2:20]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 135979298HCID 135979298, compound

Product 1

HCID 86704557HCID 86704557, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-fluoro-5-nitrophenyl)-1H-tetrazol-5(4H)-one (100 mg, 0.42 mmol, 1 equiv.), 3-hydroxyazetidine hydrochloride (55 mg, 0.5 mmol, 1.2 equiv.) and iPr2NEt (0.18 mL, 1.05 mmol, 2.5 equiv.) in 2 mL of CH3CN was refluxed for 3 days. Solvent was removed in vacuo and the residue was taken into EtOAc and washed with water. The organic layer was separated and concentrated. The residue was purified by column chromatography using a mixture of hexane/EtOAc (1:4) as eluent to give 108 mg (Yield=88%) of product as a yellow solid.

Workup

  1. temperaturewas refluxed for 3 days
  2. customSolvent was removed in vacuo
  3. washwashed with water
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography
  7. additiona mixture of hexane/EtOAc (1:4) as eluent

Sources & evidence

ORD record
ord-9cd1c1f09d4d450b897ccc43ae5faf74
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

Loading…