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Triethylamine → HCID 11998894, compound

HRID 2102745
Notes
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Reaction equation

HRID 2102745 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.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][N:35]=1>ClCCl.C1(C)C=CC=CC=1>[Cl:33][C:34]1[N:35]=[CH:36][C:37]([NH:40][C:41]([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:42])=[CH:38][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 49612732-chloro-5-isocyanatopyridineHCID 57803070Rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 11998894HCID 11998894, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 6344
Dichloromethane
Solvent

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 (74.3 ul, 0.53 mmol) (Aldrich), followed by the addition of solution of 2-chloro-5-isocyanato-pyridine (1.28 mL, 0.26 mmol) in toluene (from Example 66a supra). The mixture was stirred at room temperature for 30 minutes. 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 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 (6-chloro-pyridin-3-yl)-amide as a white solid. (Yield 32 mg, 28.3%).

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 Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-bb5a4ffcbee34a42a0a8d76a8df528f3
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576082B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes