Propylamine → HCID 70170662, compound

HRID 2171061Notes

Reaction equation

HRID 2171061 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]([OH:10])=O.Cl.C[N:31](C)[CH2:32][CH2:33][CH2:34]N=C=NCC.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.C(N)CC>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:31][CH2:32][CH2:33][CH3:34])=[O:10]

Participants

8

Reactant 5

HCID 7852PropylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67467711HCID 67467711, compound

Product 1

HCID 70170662HCID 70170662, compoundYield 37.4%

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 (0.1 mL, 0.75 mmol) and 1-hydroxybenzotriazole hydrate (HOBT) (76.5 mg, 0.50 mmol) and stirred for 10 min. To this propylamine (59 mg, 1.0 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, 0-40% ethyl acetate in pet ether) afforded the title compound as a solid (40 mg, 36%).

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, 0-40% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-a685ed20b3944f99af10746694b3bb43
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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