Dicyclohexylcarbodiimide → (S)-Tetrahydro-furan-3-carboxylic acid {4-[4-(diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-amide

HRID 1927597Notes

Reaction equation

HRID 1927597 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[C:4]([F:28])[CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.[O:44]1[CH2:48][CH2:47][C@H:46]([C:49](O)=[O:50])[CH2:45]1>ClCCCl>[CH2:20]([N:17]([CH2:18][CH3:19])[C:15]([CH:14]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:49]([C@H:46]3[CH2:47][CH2:48][O:44][CH2:45]3)=[O:50])=[CH:3][C:4]=2[F:28])[CH2:9][CH2:10]1)=[O:16])[CH3:21]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 40784874(3S)-oxolane-3-carboxylic acidHCID 581573072-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N,N-diethyl-2-phenyl-acetamide

Product 1

HCID 58870766(S)-Tetrahydro-furan-3-carboxylic acid {4-[4-(diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-amideYield 51.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N,N-diethyl-2-phenyl-acetamide (0.30 mmol) and DCC (1.0 mmol) in DCE (10 mL) was stirred at rt for 1 h, then was treated with (S)-tetrahydro-furan-3-carboxylic acid (1.0 mmol), and was stirred at rt for 16 h. The mixture was concentrated, and the residue was purified by PTLC to provide the title compound (74 mg, 51%). MS (ESI): mass calcd. for C27H35FN4O3, 482.27. m/z found, 483.4 [M+H]+. 1H NMR (CDCl3): 7.75-7.60 (m, 1H), 7.55-7.26 (m, 5H), 7.10-7.00 (m, 1H), 6.84 (t, J=9.0, 1H), 4.21 (s, 1H), 4.05-3.72 (m, 4H), 3.50-3.10 (m, 4H), 3.10-2.95 (m, 5H), 2.73-2.60 (m, 4H), 2.28-2.18 (m, 2H), 1.14-1.02 (m, 6H).

Workup

  1. stirringwas stirred at rt for 16 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by PTLC

Sources & evidence

ORD record
ord-d3fcf88553c545d5b90388f41f714809
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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