Triethylamine → HCID 11999358, compound

HRID 2102768Notes

Reaction equation

HRID 2102768 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.[N:33]([C:36]1[CH:41]=[CH:40][C:39]([N:42]2[C:46](=[O:47])[CH:45]=[CH:44][C:43]2=[O:48])=[CH:38][CH:37]=1)=[C:34]=[O:35]>ClCCl>[O:48]=[C:43]1[CH:44]=[CH:45][C:46](=[O:47])[N:42]1[C:39]1[CH:40]=[CH:41][C:36]([NH:33][C:34]([N:14]2[CH2:15][CH2:16][CH2:17][CH:12]([C:6]3([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=4)[NH:8][C:7]3=[O:11])[CH2:13]2)=[O:35])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1299754-Maleimidophenyl isocyanateHCID 57803070Rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 11999358HCID 11999358, compoundYield 28.3%

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 (80 mg, 0.21 mmol) (from Example 25a supra) in dichloromethane (3 mL) was added triethylamine (32.4 mg, 0.32 mmol) (Aldrich), followed by the addition of 1-(4-isocyanato-phenyl)-pyrrole-2,5-dione (50 mg, 0.23 mmol) (Fluka). The mixture was stirred at room temperature for 0.5 hour. The mixture was partitioned between dichlormethane and water. The aqueous layer was extracted with dichlormethane. The combined organic layer was washed with water, brine, dried over MgSO4 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 [4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl)-amide as a white solid (Yield 35 mg, 28%).

Workup

  1. customThe mixture was partitioned between dichlormethane and water
  2. extractionThe aqueous layer was extracted with dichlormethane
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-30c7b99606864d04b71b637d74bde96a
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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