1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500674, compound

HRID 632940Notes

Reaction equation

HRID 632940 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.CCN=C=NCCCN(C)C.[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[O:38][C:39]([C:50]([F:53])([F:52])[F:51])=[C:40]([C:42]([NH:44][CH2:45][CH2:46][C:47](O)=[O:48])=[O:43])[N:41]=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:18])[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:47](=[O:48])[CH2:46][CH2:45][NH:44][C:42]([C:40]3[N:41]=[C:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[Cl:30])[O:38][C:39]=3[C:50]([F:51])([F:53])[F:52])=[O:43])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1179200333-{[2-(2-Chlorophenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionic acidHCID 178500653HCID 178500653, compound

Product 1

HCID 178500674HCID 178500674, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Trans-[4-(4-aminophenyl)cyclohexyl]acetic acid methyl ester (70 mg, 0.28 mmol), EDCI (135.6 mg, 0.71 mmol), 3-{[2-(2-chlorophenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionic acid (123.2 mg, 0.34 mmol), HOBt (57.4 mg, 0.23 mmol) and ethyldiisopropylamine (128.3 mg, 0.99 mmol) dissolved in dichloromethane (15 mL) were 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 by silica gel column chromatography to obtain the desired compound (165 mg, 99%) 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 by silica gel column chromatography

Sources & evidence

ORD record
ord-e8f1a8bd567b4fa183ab053584cf686f
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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