1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500680, compound

HRID 632958Notes

Reaction equation

HRID 632958 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]=[CH:41][CH:40]=[C:39]([Cl:43])[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.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:49]([C:47]3[N:48]=[C:44]([C:38]4[C:37]([Cl:36])=[CH:42][CH:41]=[CH:40][C:39]=4[Cl:43])[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 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 117920278HCID 117920278, compoundHCID 178500667HCID 178500667, compound

Product 1

HCID 178500680HCID 178500680, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-{4-[4-(3-aminopropionylamino)phenyl]cyclohexyl}acetic acid methyl ester HCl salt (380 mg, 1.071 mmol), EDCI (513.3 mg, 2.678 mmol), 2-(2,6-dichlorophenyl)-5-trifluoromethyloxazole-4-carboxylic acid (366.61 mg, 1.125 mmol), HOBt (217.09 mg, 1.607 mmol) and ethyldiisopropylamine (485.63 mg, 3.749 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 solvent was removed. Column chromatography was conducted on the crude material to obtain trans-{4-[4-(3-{[2-(2,6-dichlorophenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (609 mg, 91%).

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, and solvent
  5. customwas removed

Sources & evidence

ORD record
ord-fa8a50e51d164dc393a3611b4f32f83e
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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