2-Methoxyethylamine → HCID 25141526, compound

HRID 508125Notes

Reaction equation

HRID 508125 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:31]([F:34])([F:33])[F:32])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]([NH:26][CH2:27][C:28](O)=[O:29])=[O:25])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CC(C)(C)C(Cl)=O.[CH3:42][O:43][CH2:44][CH2:45][NH2:46].C(N(CC)CC)C>ClCCl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:31]([F:33])([F:34])[F:32])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]([NH:26][CH2:27][C:28]([NH:46][CH2:45][CH2:44][O:43][CH3:42])=[O:29])=[O:25])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 68512729HCID 68512729, compound2×

Product 1

HCID 25141526HCID 25141526, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N—[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]carbonyl]glycine (i.e. the title product of Step B) (100 mg) and pyridine (0.019 mL) in dichloromethane (3 mL) was added trimethylacetyl chloride (0.029 mL). The reaction mixture was stirred at room temperature for 2 h, and then 2-methoxyethylamine (0.11 mL) and triethylamine (0.68 mL, 5.0 mmol) were added. The reaction mixture was stirred at room temperature overnight, quenched with water, extracted with dichloromethane, washed with brine, dried with anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel using hexanes/ethyl acetate (3:2 to 1:4) as eluent to afford the title compound, a compound of the present invention, as a white solid (71 mg, 0.13 mmol, 65% yield).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e8f81da77d894a18a2357e10b4b75e52
Source dataset
uspto-grants-2015_08
Patent number
US09095138B2

Reaction notes

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