1-Methylpiperazine → HCID 70571655, compound

HRID 2403601Notes

Reaction equation

[N+](C1C=CC([N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][N:27]([C:29](=[O:39])[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH3:28])[CH:21]=3)=[CH:16][CH:15]=2)[C:11](=[O:13])[O-])=CC=1)([O-])=O.C[CH2:41][N:42]([CH:46]([CH3:48])C)[CH:43]([CH3:45])C.C[N:50]1CCNCC1>ClCCl>[CH3:28][N:27]([CH2:26][C:22]1[CH:21]=[C:20]([C:17]2[CH:16]=[CH:15][C:14]([NH:10][C:11]([N:50]3[CH2:45][CH2:43][N:42]([CH3:41])[CH2:46][CH2:48]3)=[O:13])=[CH:19][CH:18]=2)[CH:25]=[CH:24][CH:23]=1)[C:29](=[O:39])[CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:37])([CH3:38])[CH3:36]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 4-nitrophenyl(3′-{[{[(tert-butoxycarbonyl)amino]acetyl}(methyl)amino]methyl}biphenyl-4-yl)carbamate (150 mg), DIPEA (36 mg), and dichloromethane (3 ml) was added 1-methylpiperazine (28 mg), followed by stirring at 50° C. for 5 hours. The reaction mixture was subjected to liquid separation with CHCl3-water, and the aqueous layer was extracted with CHCl3. The combined organic layer was dried over Na2SO4, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3) to obtain tert-butyl (2-{methyl[(4′-{[(4-methylpiperazin-1-yl)carbonyl]amino}biphenyl-3-yl)methyl]amino}-2-oxoethyl)carbamate (132 mg) as a pale yellow oil.

Workup

customThe reaction mixture was subjected to liquid separation with CHCl3-water
extractionthe aqueous layer was extracted with CHCl3
dry with materialThe combined organic layer was dried over Na2SO4
customthe solvent was evaporated
customThe obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3)

Sources & evidence

ORD record: ord-2ad1b65bc1f7485fa2bf0790b9d826d9
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802679B2

Reaction notes

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