1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500675, compound

HRID 632952Notes

Reaction equation

HRID 632952 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.[F:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1[O:44][C:45]([C:51]([F:54])([F:53])[F:52])=[C:46]([C:48](O)=[O:49])[N:47]=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:48]([C:46]3[N:47]=[C:43]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[F:36])[O:44][C:45]=3[C:51]([F:54])([F:53])[F:52])=[O:49])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 117920156HCID 117920156, compoundHCID 178500667HCID 178500667, compound

Product 1

HCID 178500675HCID 178500675, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Trans-{4-[4-(3-aminopropionylamino)phenyl]cyclohexyl}acetic acid methyl ester HCl salt (50 mg, 0.14 mmol), EDCI (67.5 mg, 0.35 mmol), 2-(2-fluorophenyl)-5-trifluoromethyloxazole-4-carboxylic acid (46.5 mg, 0.17 mmol), HOBt (28.6 mg, 0.2 mmol) and ethyldiisopropylamine (63.9 mg, 0.5 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 by a silica gel column chromatography to obtain trans-{4-[4-(3-{[2-(2-fluorophenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (73 mg, 90%) 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 a silica gel column chromatography

Sources & evidence

ORD record
ord-f82b9ad1fb304189b1060bb533d86af4
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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