Triethylamine → HCID 67052435, compound

HRID 599434Notes

Reaction equation

HRID 599434 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(N(CC)CC)C.Cl[CH2:21][C:22]1[N:23]([CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C:24]2[C:33]3[N:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1>CN(C=O)C.O>[O:7]=[C:6]1[C:5]2[C:4](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:12])[N:2]1[O:1][CH2:21][C:22]1[N:23]([CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:43])([CH3:42])[CH3:44])[C:24]2[C:33]3[N:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 66958197HCID 66958197, compound

Product 1

HCID 67052435HCID 67052435, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-Hydroxyphthalimide (2.06 g, 12.7 mmol) and triethylamine (2.40 mL, 17.3 mmol) were added to a solution of tert-butyl 3-[2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propylcarbamate (prepared as described in Parts A-D of Example 92, 11.5 mmol) in DMF (60 mL). The reaction was allowed to stir overnight at room temperature. The resulting orange suspension was diluted with water (40 mL) and the solid was isolated by filtration, washed with water (2×30 mL), and dried in a vacuum oven at 70° C. to afford 4.86 g of tert-butyl 3-(2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propylcarbamate as a white solid. The material was used without further purification in the next step.

Workup

  1. customthe solid was isolated by filtration
  2. washwashed with water (2×30 mL)
  3. customdried in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-566f66216e5f402690181bdee829852f
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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