Piperazine → HCID 17952587, compound

HRID 456435Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.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.CC(C)([O-])C.[Na+]>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:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

The compound of Step 1 (600 mg, 1.68 mmol), piperazine (174 mg, 2.02 mmol), Pd2(dba)3 (77 mg, 0.084 mmol), BINAP (157 mg, 0.252 mmol), and sodium tert-butoxide (226 mg, 2.35 mmol) were mixed together and degassed followed by the addition of toluene (20 mL). The mixture was heated to 100° C. for about 16 hours. The mixture was cooled to r.t, and then diluted with ether (50 mL), filtered through celite and concentrated. The residue was subjected to SCX purification, and the resultant oil was chromatographed on silica gel (MeOH (NH3 2M)/DCM) to give the final compound (311. mg, 51%) as a yellow foam. MS found 362.3, M+1

Workup

customdegassed
additionfollowed by the addition of toluene (20 mL)
temperatureThe mixture was cooled
additiondiluted with ether (50 mL)
filtrationfiltered through celite
concentrationconcentrated
customThe residue was subjected to SCX purification
customthe resultant oil was chromatographed on silica gel (MeOH (NH3 2M)/DCM)

Sources & evidence

ORD record: ord-044626455f69469698a67edf6810ee00
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186715B2

Reaction notes

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