HCID 841789, compound → HCID 16667284, compound

HRID 1927607Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])=[C:4]([F:16])[CH:3]=1.[CH2:17]([NH:19][C:20](=[O:34])[CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:18].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.CC(C)([O-])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]>[CH2:11]([CH:10]([CH2:13][CH3:14])[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([N:25]2[CH2:24][CH2:23][N:22]([CH:21]([C:20](=[O:34])[NH:19][CH2:17][CH3:18])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:27][CH2:26]2)=[CH:3][C:4]=1[F:16])=[O:15])[CH3:12]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of N-(4-bromo-2-fluoro-phenyl)-2-ethyl-butyramide (20 mg, 0.07 mmol), N-ethyl-2-phenyl-2-piperazin-1-yl-acetamide (18 mg, 0.07 mmol), Pd2(dba)3 (10 mg), and 2-(dicyclohexylphosphino)biphenyl (1 mg) in toluene was added sodium tert-butoxide (20 mg). The mixture was heated in a focused microwave at 110° C. for 1.5 h. The crude reaction mixture was purified by reverse phase HPLC (Agilent method) to provide the title compound (4 mg, 13%). MS (ESI): mass calcd. for C26H35FN4O2, 454.27. m/z found, 455.4 [M+H]+. 1H NMR (CDCl3): 8.10 (dd, J=9.6, 8.9, 1H), 7.38-7.30 (m, 3H), 7.14-6.99 (m, 2H), 6.68-6.59 (m, 2H), 3.88 (s, 1H), 3.43-3.29 (m, 2H), 3.21-3.10 (m, 4H), 2.66-2.55 (m, 4H), 2.12-2.00 (m, 1H), 1.79-1.67 (m, 2H), 1.66-1.47 (m, 2H), 1.18 (t, J=7.2, 3H), 0.98 (t, J=7.4, 6H).

Workup

customThe crude reaction mixture
customwas purified by reverse phase HPLC (Agilent method)

Sources & evidence

ORD record: ord-dbcd495a82c3441697939674591dd051
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183239B2

Reaction notes

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