Triethylamine → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-[N-(ethoxycarbonyl)amino]phenyl]piperidin-3-ol

HRID 1392392Notes

Reaction equation

HRID 1392392 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[NH2:34])[CH2:24][CH:23]2[OH:35])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].C(N(CC)CC)C.Cl[C:44]([O:46][CH2:47][CH3:48])=[O:45]>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[NH:34][C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:24][CH:23]2[OH:35])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 693129984-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-ol

Product 1

HCID 693130064-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-[N-(ethoxycarbonyl)amino]phenyl]piperidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexane carbonyl]amino]-1-(2-aminophenyl)piperidin-3-one (0.9 g) obtained in Step 2 of Example 43 in 20 ml of dichloromethane was cooled to 0° C. 0.54 ml of triethylamine and 0.37 ml of ethyl chloroformate were added to the reaction mixture, which was then stirred for about 3 hours at room temperature. 20 ml of ice water was added to the reaction mixture. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 600 mg of the titled compound.

Workup

  1. customThe resulting organic layer was dried
  2. concentrationconcentrated on sodium sulfate
  3. customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record
ord-661c0c10a3654b27ab3e4bfa13dd07b3
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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