Triethylamine → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-amino-5-fluorophenyl)piperidin-3-ol

HRID 1392398Notes

Reaction equation

HRID 1392398 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12].[F:30][C:31]1[CH:36]=CC(F)=[CH:33][C:32]=1[N+]([O-])=O.C([N:43]([CH2:46][CH3:47])CC)C>C(O)C>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([C:33]3[CH:32]=[C:31]([F:30])[CH:36]=[CH:47][C:46]=3[NH2:43])[CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 677672,5-DifluoronitrobenzeneHCID 115679944-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride

Product 1

HCID 693155514-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-amino-5-fluorophenyl)piperidin-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride (6.0 g) obtained in Step 2 of Example 1 in 50 ml of ethanol, were added 3.7 ml 2,5-difluoronitrobenzene and 4.8 ml triethylamine. The reaction mixture was refluxed overnight and concentrated. The resulting residue was filtered and dried to give 7.2 g of the titled compound.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated
  3. filtrationThe resulting residue was filtered
  4. customdried

Sources & evidence

ORD record
ord-354f4bb93c934e1aaf7909d276f6e34a
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

Loading…