Nitrogen → HCID 178490315, compound

HRID 2253308Notes

Reaction equation

HRID 2253308 reaction equation
N#N.Br[C:4]1[C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=3)[NH:16][C:12]=2[C:11]2[C:10](=[O:27])[N:9]([CH2:28][CH2:29][CH2:30][N:31]([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([O:49][CH3:50])[CH:42]=3)[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:8](=[O:51])[C:7]([CH3:53])([CH3:52])[C:6]=2[CH:5]=1.CO[C:56]1[CH:63]=[CH:62][C:59]([CH2:60][NH2:61])=[CH:58][CH:57]=1.C[C:65]([O-:68])(C)C.[Na+]>C1COCC1.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=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:50][O:49][C:43]1[CH:42]=[C:41]([CH2:40][CH2:39][N:31]([CH2:30][CH2:29][CH2:28][N:9]2[C:8](=[O:51])[C:7]([CH3:52])([CH3:53])[C:6]3[CH:5]=[C:4]([NH:61][CH:60]([O:68][CH3:65])[C:59]4[CH:58]=[CH:57][CH:56]=[CH:63][CH:62]=4)[C:13]4[N:14]=[C:15]([C:17]5[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=5)[NH:16][C:12]=4[C:11]=3[C:10]2=[O:27])[C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH:46]=[CH:45][C:44]=1[O:47][CH3:48]

Participants

8

Reactant 4

HCID 947NitrogenHCID 754524-MethoxybenzylamineHCID 23676156Sodium t-butoxideHCID 59645483tert-Butyl {3-[4-bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-7,9-dioxo-1,6,7,9-tetrahydro-8H-imidazo[4,5-h]isoquinolin-8-yl]propyl}[2-(3,4-dimethoxyphenyl)ethyl]carbamate

Product 1

HCID 178490315HCID 178490315, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Pd2(dba)3 (5.6 mg, 5.12 μmol) and dppf (2.83 mg, 5.09 μmol) were added to a degassed (N2 for 30 min) mixture of tert-butyl {3-[4-bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-7,9-dioxo-1,6,7,9-tetrahydro-8H-imidazo[4,5-h]isoquinolin-8-yl]propyl}[2-(3,4-dimethoxyphenyl)ethyl]carbamate (780 mg, 1.02 mmol), 4-methoxybenzylamine (533 μL, 4.08 mmol) and NaOt-Bu (196 mg, 2.04 mmol) in THF (10.2 mL). The reaction mixture was stirred at 60° C. for 3 h, then was concentrated under reduced pressure. The residue was purified by flash chromatography (40-63μ silica gel; CH2Cl2:acetone 95:5) to give the title compound (542 mg, 65% yield).

Workup

  1. customa degassed
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (40-63μ silica gel; CH2Cl2:acetone 95:5)

Sources & evidence

ORD record
ord-462a8938ecdc4dcaa09f155e689e2fe8
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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