Triethylamine → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-[N-(2,5-dihydropyrrol-1-yl)amino]phenyl]piperidin-3-ol

HRID 1392394Notes

Reaction equation

HRID 1392394 reaction equation
C(OC/C=C\COC(=O)C)(=O)C.[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]([NH:24][C:25]1([C:31]([NH:33][CH:34]2[CH2:39][CH2:38][N:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[NH2:46])[CH2:36][CH:35]2[OH:47])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:23].[CH2:48]([N:50](CC)[CH2:51][CH3:52])[CH3:49]>ClCCl.CN(C)C=O>[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]([NH:24][C:25]1([C:31]([NH:33][CH:34]2[CH2:39][CH2:38][N:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[NH:46][N:50]3[CH2:51][CH:52]=[CH:49][CH2:48]3)[CH2:36][CH:35]2[OH:47])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 643799(2Z)-but-2-ene-1,4-diyl diacetateHCID 693129984-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-ol

Product 1

HCID 693156224-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-[N-(2,5-dihydropyrrol-1-yl)amino]phenyl]piperidin-3-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of cis-2-buten-1,4-diol diacetate (1.15 g) in 30 ml of dichloromethane, was added the solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-ol (1.5 g) obtained in Step 2 of Example 43 in 20 ml of dimethylformamide. 0.44 ml of triethylamine was added to the reaction mixture, which was then stirred overnight 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 0.7 g 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-47f93341a4844ddd87136e847c149cf4
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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