1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500672, compound

HRID 632956Notes

Reaction equation

HRID 632956 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]([F:57])([F:56])[C:38]1[O:42][C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[C:49]([F:52])([F:51])[F:50])=[N:40][C:39]=1[C:53](O)=[O:54].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C.C([O-])(O)=O.[Na+]>ClCCl>[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:53]([C:39]3[N:40]=[C:41]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]([F:51])([F:50])[F:52])[O:42][C:38]=3[C:37]([F:36])([F:56])[F:57])=[O:54])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1

Participants

8

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 117920199HCID 117920199, compoundHCID 178500667HCID 178500667, compound

Product 1

HCID 178500672HCID 178500672, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-{4-[4-(3-aminopropionylamino)phenyl]cyclohexyl}acetic acid methyl ester HCl salt (300 mg, 0.846 mmol), EDCI (405.23 mg, 2.114 mmol), 5-trifluoromethyl-2-(2-trifluoromethylphenyl)oxazole-4-carboxylic acid (288.68 mg, 0.888 mmol), HOBt (171.39 mg, 1.268 mmol) and ethyldiisopropylamine (383.39 mg, 2.959 mmol) were put into dichloromethane solvent (10 mL) and stirred at room temperature for 24 hours. After the reaction, aqueous NaHCO3 was added thereto, and extracted with dichloromethane. The organic layer was washed with brine, then the product was dried with anhydrous sodium sulfate, and the solvent was removed. Column chromatography was conducted on the crude material to obtain trans-{4-[4-(3-{[5-trifluoromethyl-2-(2-trifluoromethylphenyl)oxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (461 mg, 87%).

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialthe product was dried with anhydrous sodium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-19585e0343714088aa09abe1c56287f3
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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