1-Naphthalenecarbonyl chloride → (R)-Methyl 3-(1-naphthamido)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193274Notes

Reaction equation

HRID 1193274 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH2:10][C@H:9]2[NH2:15])=[O:5].CCN(C(C)C)C(C)C.[C:25]1([C:35](Cl)=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>ClCCl.C(OCC)(=O)C>[C:25]1([C:35]([NH:15][C@H:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([C:4]([O:3][CH3:2])=[O:5])[CH:7]=3)[CH2:11][CH2:10]2)=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 66700566(R)-methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride

Product 1

HCID 66799274(R)-Methyl 3-(1-naphthamido)-2,3-dihydro-1H-indene-5-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-01) (1.098 mmol, 1 eq) was dissolved in dichloromethane, and DIPEA (2.5 eq) and naphthalene-1-carboxylic acid chloride (1.0 eq) were added under a protecting gas atmosphere at 0° C. The reaction mixture was stirred for 1.5 h at RT. Then the reaction mixture was diluted with ethyl acetate, washed 1× with 10% ammonium chloride solution and 1× with sat. NaCl solution, dried over magnesium sulfate and purified by column chromatography (silica gel, cyclohexane:ethyl acetate 3:1). Yield: 58%

Workup

  1. washwashed 1× with 10% ammonium chloride solution and 1× with sat. NaCl solution
  2. dry with materialdried over magnesium sulfate
  3. custompurified by column chromatography (silica gel, cyclohexane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-615f4f9258ab44ef86da7657e880831b
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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