Cyclohexylamine → 1-cyclohexylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19566Notes

Reaction equation

HRID 19566 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7](Br)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[CH:24]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH:30][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 686984701-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 115528981-cyclohexylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (100 mg, 0.27 mmol) obtained in Example 18 was dissolved in THF (10 mL), and cyclohexylamine (132.86 mg, 0.15 mL, 1.34 mmol) was added dropwise thereto. The mixture was stirred for 12 hrs at RT, and the solvent was removed under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 25 mg of the titled compound (yield: 24%).

Workup

  1. customthe solvent was removed under a reduced pressure
  2. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fa352a66237a4e1da45c46fcb9bd6c19
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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