1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 9959240, compound

HRID 1005931Notes

Reaction equation

HRID 1005931 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=2)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.[NH2:50][CH:51]1[CH2:56][C:55]([CH3:58])([CH3:57])[NH:54][C:53]([CH3:60])([CH3:59])[CH2:52]1>C1COCC1>[Cl:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[Cl:28])[NH:19][C:18]([C:17]1[CH:16]=[CH:15][C:11]([C:12]([NH:50][CH:51]3[CH2:52][C:53]([CH3:60])([CH3:59])[NH:54][C:55]([CH3:58])([CH3:57])[CH2:56]3)=[O:14])=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:26]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 757711-HydroxybenzotriazoleHCID 22675039HCID 22675039, compound

Product 1

HCID 9959240HCID 9959240, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-benzyloxy-4-(5,6-dichloro-1H-indol-2-yl)benzoic acid (0.14 g, 0.34 mmol), prepared as in Description 19, in THF (14 ml), WSC (N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride) (0.078 g, 0.408 mmol) and 1-hydroxybenzotriazole (0.0551 g, 0.408 mmol) was refluxed for 6 h. A solution of 4-amino-2,2,6,6-tetramethylpiperidine (0.064 g, 0.408 mmol) in THF (2 ml) was added dropwise and refluxed for additional 2 h. The solvent was removed under vacuum and the residue suspended in water. The solid was filtrated and dried under vacuum. The solid was triturated with CH3CN (5 ml) to give 0.094 g (yield 45%) of the title compound as a white powder, mp=220° C.

Workup

  1. temperaturerefluxed for additional 2 h
  2. customThe solvent was removed under vacuum
  3. filtrationThe solid was filtrated
  4. customdried under vacuum
  5. customThe solid was triturated with CH3CN (5 ml)

Sources & evidence

ORD record
ord-2fc67893c38143818c532ec86126d717
Source dataset
uspto-grants-2004_09
Patent number
US06787550B1

Reaction notes

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