Isopropylamine → HCID 70171213, compound

HRID 2171060Notes

Reaction equation

HRID 2171060 reaction equation
[CH3:1][O:2][C:3]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[O:23][CH2:22]3)[C:4]=1[O:5][CH2:6][C:7]([CH3:12])([CH3:11])[C:8](O)=[O:9].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.O.O[N:50]1[C:54]2[CH:55]=CC=C[C:53]=2N=N1.C(N)(C)C>ClCCl.O>[CH3:1][O:2][C:3]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[O:23][CH2:22]3)[C:4]=1[O:5][CH2:6][C:7]([CH3:11])([CH3:12])[C:8]([NH:50][CH:54]([CH3:55])[CH3:53])=[O:9]

Participants

8

Reactant 5

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67467711HCID 67467711, compound

Product 1

HCID 70171213HCID 70171213, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 3-(2,3-dimethoxy-6-(1-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)-2,2-dimethylpropanoic acid (100 mg, 0.25 mmol) in dichloromethane (10 mL) was added 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC. HCl) (71.6 mg, 0.375 mmol), triethylamine (1 mL, 0.75 mmol) and 1-hydroxybenzotriazole hydrate (HOBT) (76.5 mg, 0.50 mmol) and stirred for 10 min. To this isopropyl amine (59 mg, 1.00 mmol) was added and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0-50% ethyl acetate in pet ether) afforded the title compound as a solid (27 mg, 27%).

Workup

  1. customthe resultant reaction mixture
  2. stirringwas stirred at RT for 16 h
  3. extractionextracted with dichloromethane (3×)
  4. washThe combined dichloromethane layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by column chromatography (silica gel, 0-50% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-5e54f03b349846d0bdd4f2273381cecf
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…