4-Methoxybenzylamine → 4-[1-(4-Methoxybenzyl)amino-5-isoquinolyl]amino-1-(tert-butoxycarbonyl)piperidine

HRID 10580

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.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]>[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:2]2[C:11]3[C:6](=[C:7]([NH:12][CH:13]4[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]4)[CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of Intermediate 84 (235 mg), 4-methoxybenzylamine (110 μl), tris(dibenzylideneacetone)dipalladium(0) (30.4 mg), 2-(di-tert-butylphosphino)biphenyl (41.0 mg) and sodium tert-butoxide (93.6 mg) in toluene (4.5 ml) was stirred at 70° C. for 1 hour. The reaction mixture was filtered through a Celite layer, and the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (270 mg).

Workup

filtrationThe reaction mixture was filtered through a Celite layer
customthe solvent was evaporated under reduced pressure
customThen, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-d189c45fbcf042a78bf55612f254a951
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094789B2

Linked notes

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