Ethanol → (rac)-N-Methyl-2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetamide

HRID 714108Notes

Reaction equation

HRID 714108 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21](O)=[O:22])[C:12]=3[CH:13]=[N:14][CH:15]=2)=[CH:6][CH:5]=1.[CH:26]([N:29](CC)C(C)C)(C)C.CN.CCO.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C1COCC1>[CH3:26][NH:29][C:21](=[O:22])[CH2:20][O:19][CH:16]1[C:12]2[CH:13]=[N:14][CH:15]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([F:25])([F:24])[F:2])=[CH:9][CH:8]=3)[C:11]=2[CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 702EthanolHCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 89846289(rac)-2-(4-(4-(Trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetic acid hydrochloride

Product 1

HCID 71811488(rac)-N-Methyl-2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetamideYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (rac)-2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetic acid hydrochloride (example 99) (70 mg, 0.19 mmol) in THF (0.6 mL) was added N,N-diisopropylethylamine (131 μL, 0.75 mmol), 8M methylamine in EtOH (47 μL, 0.38 mmol) and 1-propanephosphonic acid cyclic anhydride (284 μL, 0.47 mmol). The reaction was stirred at room temperature for 16 h. The mixture was evaporated and purified by flash chromatography (20 g SiO2, Telos-cartridge, 2 to 10% 2-propanol in CH2Cl2) to give the title compound (41 mg, 63%) as light yellow oil. MS: 351.5 (M+H+).

Workup

  1. customThe mixture was evaporated
  2. custompurified by flash chromatography (20 g SiO2, Telos-cartridge, 2 to 10% 2-propanol in CH2Cl2)

Sources & evidence

ORD record
ord-72159898075749e9b8f963a9f70592dc
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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