Water → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(3-chloro-2,2-dimethylbutyryl)aminophenyl]piperidin-3-ol

HRID 1392389Notes

Reaction equation

HRID 1392389 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].[CH2:36](N(CC)CC)C.[Cl:43][CH2:44][C:45]([CH3:50])([CH3:49])[C:46](Cl)=[O:47].O>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:46](=[O:47])[C:45]([CH3:50])([CH3:49])[CH:44]([Cl:43])[CH3:36])[CH2:24][CH:23]2[OH:35])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 693129984-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-ol

Product 1

HCID 693103664-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(3-chloro-2,2-dimethylbutyryl)aminophenyl]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-ol (4.0 g) obtained in Step 2 in 30 ml of dichloromethane was cooled to 0° C. 2.2 ml of triethylamine and 2.1 ml of 3-chloropivaloyl chloride were added dropwise to the reaction mixture, which was then stirred for about 2 hours at room temperature. 20 ml of iced water was added to the reaction mixture. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was crystallized with ethyl acetate to give 4.1 g of the titled compound.

Workup

  1. customThe resulting organic layer was dried
  2. concentrationconcentrated on sodium sulfate
  3. customThe resulting residue was crystallized with ethyl acetate

Sources & evidence

ORD record
ord-dc7fa080eb0648fc90b6bf898443dd87
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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