1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500678, compound

HRID 632954Notes

Reaction equation

HRID 632954 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:24])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:23])[CH2:20][CH2:21][NH2:22])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.CCN=C=NCCCN(C)C.[Cl:36][C:37]1[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=1[C:44]1[O:45][C:46]([C:52]([F:55])([F:54])[F:53])=[C:47]([C:49](O)=[O:50])[N:48]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>ClCCl.C([O-])(O)=O.[Na+]>[CH3:2][O:3][C:4](=[O:24])[CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:23])[CH2:20][CH2:21][NH:22][C:49]([C:47]3[N:48]=[C:44]([C:38]4[CH:39]=[CH:40][C:41]([Cl:43])=[CH:42][C:37]=4[Cl:36])[O:45][C:46]=3[C:52]([F:55])([F:54])[F:53])=[O:50])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 117920169HCID 117920169, compoundHCID 178500667HCID 178500667, compound

Product 1

HCID 178500678HCID 178500678, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of trans-{4-[4-(3-aminopropionylamino)phenyl]cyclohexyl}acetic acid methyl ester HCl salt (60 mg, 0.17 mmol), EDCI (81 mg, 0.42 mmol), 2-(2,4-dichloro-phenyl)-5-trifluoromethyl-oxazole-4-carboxylic acid (66.14 mg, 0.2 mmol), HOBt (34.27 mg, 0.25 mmol) and ethyldiisopropylamine (76.7 mg, 0.6 mmol) dissolved in dichloromethane solvent (10 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 with silica gel column chromatography to obtain the desired compound (80 mg, 75%) 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-9303acb28c2848bca9fe05e91a9f9b50
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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