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Diisopropylcarbodiimide → 1-(4-Methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic Acid [2-(1-methyl-pyrrolidin-2-yl)-ethyl]amide

HRID 1174518
Notes
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Reaction equation

HRID 1174518 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([S:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]([C:25]([OH:27])=O)[CH2:17]2)(=[O:15])=[O:14])=[CH:5][CH:4]=1.ON1C2C=CC=CC=2N=N1.CC(C)N=C=NC(C)C.[CH3:47][N:48]1[CH2:52][CH2:51][CH2:50][CH:49]1[CH2:53][CH2:54][NH2:55]>ClCCl.O>[CH3:47][N:48]1[CH2:52][CH2:51][CH2:50][CH:49]1[CH2:53][CH2:54][NH:55][C:25]([CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([S:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:14])=[O:15])[CH2:17]1)=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 687698721-(4-methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic Acid

Product 1

HCID 98703421-(4-Methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic Acid [2-(1-methyl-pyrrolidin-2-yl)-ethyl]amide
Yield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic acid (C) (900 mg, 2.35 mmol) in dichloromethane (20 cm3) was added 1-hydroxybenzotriazole (HOBT, 0.48 g, 3.53 mmol) and 1,3-diisopropylcarbodidiimide (DIC, 0.55 cm3, 3.53 mmol). This was left to stir at room temperature for 5 min, before adding 2-(1-methyl-pyrrolidin-2-yl)-ethylamine (0.342 cm3, 2.35 mmol). The reaction was stirred for 16 h at room temperature before water (60 cm3) was added followed by dichloromethane (60 cm3). The resulting mixture was then shaken and the organic layer was washed with water (40 cm3), saturated aqueous sodium bicarbonate solution (40 cm3), water again (40 cm3) and then saturated aqueous sodium chloride solution (50 cm3) before the organic portion was dried over sodium sulfate, It was then evaporated under reduced pressure to afford the title compound (1) (800 mg, 1.62 mmol, 69%), positive ion ESI (M+H)+ 494.6.

Workup

  1. waitThis was left
  2. additionwas added
  3. stirringThe resulting mixture was then shaken
  4. washthe organic layer was washed with water (40 cm3), saturated aqueous sodium bicarbonate solution (40 cm3), water again (40 cm3)
  5. dry with materialsaturated aqueous sodium chloride solution (50 cm3) before the organic portion was dried over sodium sulfate, It
  6. customwas then evaporated under reduced pressure

Sources & evidence

ORD record
ord-4ef310abf07b47d4a52042046521f4af
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07838518B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes