Pentanoyl chloride, 4-methyl- → 4-Methyl-pentanoic acid {4-[4-(ethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-amide

HRID 1927612Notes

Reaction equation

HRID 1927612 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:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15]([NH:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[C:4]([F:26])[CH:3]=1.[CH3:27][CH:28]([CH3:34])[CH2:29][CH2:30][C:31](Cl)=[O:32]>C(Cl)Cl>[CH2:18]([NH:17][C:15]([CH:14]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:31](=[O:32])[CH2:30][CH2:29][CH:28]([CH3:34])[CH3:27])=[CH:3][C:4]=2[F:26])[CH2:9][CH2:10]1)=[O:16])[CH3:19]

Participants

4

Reactant 2

HCID 170008Pentanoyl chloride, 4-methyl-HCID 669319332-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N-ethyl-2-phenyl-acetamide

Product 1

HCID 166666824-Methyl-pentanoic acid {4-[4-(ethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-amideYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N-ethyl-2-phenyl-acetamide (44 mg, 0.12 mmol) in DCM (2 mL) was treated with 4-methylvaleroyl chloride (20 mg, 0.15 mmol) followed by TEA (21 μL, 0.15 mmol). After 16 h, the mixture was purified directly by PTLC to give a beige solid (53 mg, 94%). MS (ESI): mass calcd. for C26H35FN4O2, 454.59; m/z found, 455.5 [M+H]+. 1H NMR (CDCl3): 7.38-7.28 (m, 5H), 7.10-7.04 (m, 2H), δ 7.00 (br s, 1H), 6.86 (t, J=9.0, 1H), 3.88 (s, 1H), 3.40-3.31 (m, 3H), 3.07-3.06 (m, 4H), 2.61-2.57 (m, 4H), 2.34-2.31 (m, 3H), 1.62-1.59 (m, 2H), 1.16 (t, J=7.2, 3H), 0.93 (d, J=6.1, 6H).

Workup

  1. customthe mixture was purified directly by PTLC

Sources & evidence

ORD record
ord-14c3f7472cd84bd9b557bedadebc680e
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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