1-Methylpiperazine → HCID 58109144, compound

HRID 2037514Notes

Reaction equation

[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(O[Na])(C)(C)C>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].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([N:31]3[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (400 mg, 0.96 mmol), 1-methylpiperazine (100 mg, 1.0 mmol), t-BuONa (129 mg, 1.34 mmol), Pd2(dba)3 (9 mg, 0.01 mmol), BINAP (6 mg, 0.01 mmol) in toluene. was heated to 80° C. and stirred overnight. Then the reaction mixture was concentrated to afford the residue, which was purified by preparative TLC to give (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(4-methylpiperazin-1-yl)phenyl)ethyl)-1,3-oxazinan-2-one (162 mg, 0.4 mmol). LC-MS Method 2 tR=1.77, min, m/z=438; 1H NMR (CD3OD) 1.50 (m, 3H), 2.20 (m, 2H), 2.30 (m, 3H), 2.35 (m, 1H), 2.60 (m, 6H), 3.00 (m, 1H), 3.10 (m, 4H), 5.00 (m, 2H), 5.45 (m, 1H), 5.65 (m, 1H), 6.70 (m, 2H), 6.80 (m, 2H), 7.05 (m, 2H), 7.25 (m, 2H).

Workup

concentrationThen the reaction mixture was concentrated
customto afford the residue, which
customwas purified by preparative TLC

Sources & evidence

ORD record: ord-3df2e15676d44683b83b9ba1944aba75
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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