METHYL PHENYL-PIPERAZIN-1-YL-ACETATE → HCID 16665205, compound

HRID 1927618Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Br[C:19]1[CH:32]=[CH:31][C:22]([C:23]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:24])=[CH:21][C:20]=1[F:33].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:17])[CH:4]([N:5]1[CH2:6][CH2:7][N:8]([C:19]2[CH:32]=[CH:31][C:22]([C:23](=[O:24])[NH:25][CH:26]([CH2:27][CH3:28])[CH2:29][CH3:30])=[CH:21][C:20]=2[F:33])[CH2:9][CH2:10]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of phenyl-piperazin-1-yl-acetic acid methyl ester (80 mg, 0.4 mmol), 4-bromo-N-(1-ethyl-propyl)-3-fluoro-benzamide (prepared as described in Example 113, Step A; 150 mg, 0.5 mmol), Pd2(dba)3 (6 mg, 0.007 mmol), X-Phos (3 mg, 0.007 mmol), and NaOtBu (67 mg, 0.9 mmol) in toluene (5 mL) was heated at 100° C. for 18 h. The solids were removed by filtration and the filtrate was concentrated to give an oil, which was purified by PTLC to give a beige solid (9 mg, 6%). MS (ESI): mass calcd. for C25H32FN3O3, 441.54; m/z found, 442.5 [M+H]+. 1H NMR (CDCl3): 7.46-7.43 (m, 4H), 7.38-7.33 (m, 3H), 6.90 (t, J=8.3, 1H), 5.66 (d, J=8.5, 1H), 4.07 (s, 1H), 3.70 (s, 3H), 3.20-3.18 (m, 4H), 2.65-2.63 (m, 4H), 1.68-1.55 (m, 3H), 1.49-1.42 (m, 2H), 0.93 (t, J=7.4, 6H).

Workup

customThe solids were removed by filtration
concentrationthe filtrate was concentrated
customto give an oil, which
customwas purified by PTLC

Sources & evidence

ORD record: ord-eb1ad8785ec44a18ad40cd2e83741036
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183239B2

Reaction notes

Loading…