1-Acetylpiperazine → HCID 67352325, compound

HRID 1672772Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH2:17][C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]3[N:18]=[C:19]([NH:22][CH2:23][CH3:24])[N:20]=[CH:21][C:10]=3[C:9]2=[O:25])[CH:7]=1.[C:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])[CH3:27].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.C(O)(C)(C)C.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]>[C:26]([N:29]1[CH2:34][CH2:33][N:32]([C:2]2[CH:7]=[C:6]([N:8]3[CH2:17][C@H:16]4[N:12]([CH2:13][CH2:14][CH2:15]4)[C:11]4[N:18]=[C:19]([NH:22][CH2:23][CH3:24])[N:20]=[CH:21][C:10]=4[C:9]3=[O:25])[CH:5]=[N:4][CH:3]=2)[CH2:31][CH2:30]1)(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 21 (90.0 mg, 0.223 mmol) obtained in Example 21 was dissolved in a mixed solvent of 1,4-dioxane (4 mL) and tert-butyl alcohol (2 mL), and the mixture was stirred at 80° C. for 1.5 hours after adding 1-acetylpiperazine (57.0 mg, 0.446 mmol), tris(dibenzylideneacetone)dipalladium (41.0 mg, 0.0446 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (53.0 mg, 0.134 mmol), and sodium tert-butoxide (43.0 mg, 0.446 mmol). The mixture was filtered through sellite, and the residue obtained by concentrating the filtrate was purified by silica gel column chromatography to give the title compound (Compound 40) (34.0 mg, 34%).

Workup

filtrationThe mixture was filtered through sellite
customthe residue obtained
concentrationby concentrating the filtrate
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-bc4b9ef4e366423c999976ea41b34dbd
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

Loading…