Methylamine → HCID 67468017, compound

HRID 2171049Notes

Reaction equation

HRID 2171049 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])[CH2:23][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.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.CN>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])[CH2:23][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

8

Reactant 5

HCID 6329MethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67466869HCID 67466869, compound2×

Product 1

HCID 67468017HCID 67468017, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 3-[2,3-Dimethoxy-6-(1-oxo-indan-5-yl)-phenoxy]-2,2-dimethyl-propionic acid (Compound 205) (100 mg, 0.260 mmol) in dichloromethane, were added 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (75 mg, 3.90 mmol), 1-Hydroxybenzotriazole hydrate (HOBT) (80 mg, 0.520 mmol) and triethylamine (0.1 mL, 0.9814 mmol) and 1M methylamine solution (0.4 mL, 0.520 mmol) and the resultant reaction mixture was stirred at 16 h at room temperature. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-40% ethyl acetate in pet ether) afforded the title compound as a solid.

Workup

  1. customthe resultant reaction mixture
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined dichloromethane layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (silica gel, 0-40% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-3a33af526120481e90238778f57d9eb4
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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