1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500668, compound

HRID 632948Notes

Reaction equation

HRID 632948 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:22])[CH2:19][CH2:20][NH2:21])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.CCN=C=NCCCN(C)C.[Cl:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40]([C:45](O)=[O:46])=[CH:39]2.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>ClCCl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:22])[CH2:19][CH2:20][NH:21][C:45]([C:40]3[NH:41][C:42]4[C:38]([CH:39]=3)=[CH:37][C:36]([Cl:35])=[CH:44][CH:43]=4)=[O:46])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 178500666HCID 178500666, compound

Product 1

HCID 178500668HCID 178500668, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of trans-{4-[4-(3-aminopropionylamino)phenyl]cyclohexyl}acetic acid methyl ester (50 mg, 0.16 mmol), EDCI (75.26 mg, 0.39 mmol), 5-chloro-1H-indole-2-carboxylic acid (36.86 mg, 0.19 mmol), HOBt (31.8 mg, 0.24 mmol) and ethyldiisopropylamine (71.2 mg, 0.6 mmol) dissolved in dichloromethane solvent (10 mL) was stirred for 24 hours. The reaction mixture was diluted with aqueous NaHCO3 and extracted with dichloromethane. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was purified with silica gel column chromatography to obtain the desired compound (75 mg, 96%) as a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-9da42b242a29499fba78307b39cb9b34
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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