Methylamine → HCID 70171259, compound

HRID 2171058Notes

Reaction equation

HRID 2171058 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.[CH3:30][N:31](C)CCCN=C=NCC.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.CN.C1COCC1>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]([CH3:12])([CH3:11])[C:8]([NH:31][CH3:30])=[O:9]

Participants

9

Reactant 6

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67467711HCID 67467711, compound

Product 1

HCID 70171259HCID 70171259, compoundYield 50%

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, 0.259 mmol) in dichloromethane (10 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (74 mg, 0.388 mmol), triethylamine (0.1 mL, 0.77 mmol) and 1-hydroxybenzotriazole hydrate (HOBt) (79 mg, 0.518 mmol) and stirred for 10 min. To this methyl amine solution in THF (0.518 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, 0-80% ethyl acetate in pet ether) afforded the title compound as a solid (50 mg, 50%).

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, 0-80% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-a08a8ee5087742c2ab3ae3e6fdd8c6bd
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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