Triethylamine → Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-1-carboxylic acid (2-methoxy-phenyl)-amide

HRID 2102712Notes

Reaction equation

HRID 2102712 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]=[C:42]=[O:43]>ClCCl>[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42]([N:14]1[CH2:15][CH2:16][CH2:17][CH:12]([C:6]2([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:13]1)=[O:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 57803070Rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 11998416Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-1-carboxylic acid (2-methoxy-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one (50 mg, 0.13 mmol) (from Example 25a supra) in dichloromethane (3 mL) was added triethylamine (20 mg, 0.19 mmol) (Aldrich), followed by the addition of 2-methoxyphenyl isocyanate (24 mg, 0.16 mmol) (Aldrich). The mixture was stirred at room temperature for 30 mins. The mixture was partitioned between dichlormethane and water. The aqueous layer was extracted with dichlormethane. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography to give rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (2-methoxy-phenyl)-amide as a white solid. (Yield 45 mg, 64%).

Workup

  1. customThe mixture was partitioned between dichlormethane and water
  2. extractionThe aqueous layer was extracted with dichlormethane
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-bc20a57b52f74161882d7e97ccd35cad
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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