Acetyl chloride → 1-acetylamino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester

HRID 19561Notes

Reaction equation

HRID 19561 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH2:31])[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][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])[CH3:2].[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH:31][C:32](=[O:34])[CH3:33])[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][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 115967791-amino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 117194701-acetylamino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester (30 mg, 0.07 mmol) prepared in Example 21 was dissolved in dichloromethane (10 mL), and acetyl chloride (30.15 mg, 0.37 mmol) and triethylamine (40 mg, 0.37 mmol) were added thereto in order at 0° C. The mixture was stirred for 24 hrs at RT, washed with saturated saline and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 15 mg of the titled compound (yield: 45%).

Workup

  1. customat 0° C
  2. washwashed with saturated saline
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3587d7fa1fb143fcbf845fc490cfb644
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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