Diisopropylethylamine → 3-Diethylamino-N-{4-[4-(ethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-propionamide

HRID 1927613Notes

Reaction equation

HRID 1927613 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.Cl.[CH2:28]([N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][C:33](O)=[O:34])[CH3:29].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:28]([N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][C:33]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:15](=[O:16])[NH:17][CH2:18][CH3:19])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:10][CH2:9]2)=[C:4]([F:26])[CH:3]=1)=[O:34])[CH3:29]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 3084241N,N-diethyl-beta-alanine hydrochlorideHCID 669319332-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N-ethyl-2-phenyl-acetamide

Product 1

HCID 166667293-Diethylamino-N-{4-[4-(ethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-propionamideYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N-ethyl-2-phenyl-acetamide (22 mg, 0.06 mmol), 3-diethylaminopropionic acid hydrochloride (13 mg, 0.07 mmol) and PyBroP (34 mg, 0.07 mmol) in DCM (2 mL) was treated with iPr2NEt (0.032 mL, 0.19 mmol). After 18 h, the mixture was washed with satd. aq. NaHCO3 and brine, dried (MgSO4), and concentrated to give an oil, which was purified by PTLC to give a beige solid (17 mg, 56%). MS (ESI): mass calcd. for C27H38FN5O2, 483.62. m/z found, 484.4 [M+H]+. 1H NMR (CDCl3): 11.15 (s, 1H), 7.38-7.37 (m, 1H), 7.36-7.35 (m, 1H), 7.33-7.32 (m, 3H), 7.31-7.28 (m, 1H), 7.13-7.09 (m, 2H), 6.85 (t, J=9.0, 1H), 3.88 (s, 1H), 3.38-3.33 (m, 2H), 3.06-3.04 (m, 4H), 2.79-2.76 (m, 1H), 2.69-2.65 (m, 4H), 2.59-2.58 (m, 4H), 2.50-2.47 (m, 1H), 1.40-1.38 (m, 1H), 1.35-1.32 (t, J=7.3, 1H), 1.77-1.22 (m, 9H).

Workup

  1. washthe mixture was washed with satd
  2. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  3. concentrationconcentrated
  4. customto give an oil, which
  5. customwas purified by PTLC

Sources & evidence

ORD record
ord-1753f45cd24843b29b31221035a32012
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

Loading…