1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500670, compound

HRID 632946Notes

Reaction equation

HRID 632946 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.[C:35]1([CH3:53])[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]1[CH:45]=[C:44]([C:46](O)=[O:47])[C:43]([C:49]([F:52])([F:51])[F:50])=[N:42]1.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:46]([C:44]3[C:43]([C:49]([F:52])([F:51])[F:50])=[N:42][N:41]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[CH3:53])[CH:45]=3)=[O:47])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66678096HCID 66678096, compoundHCID 178500666HCID 178500666, compound

Product 1

HCID 178500670HCID 178500670, compoundYield 91%

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), 1-o-tolyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (51 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 (82 mg, 91%) 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-13050475a23c4e90941c35e770866385
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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