Triethylamine → HCID 67052384, compound

HRID 599430Notes

Reaction equation

HRID 599430 reaction equation
C(N(CC)CC)C.[OH:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].[NH2:20][C:21]1[C:30]2[N:31]=[C:32]([CH2:43]Cl)[N:33]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[C:29]=2[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=1>CN(C=O)C>[NH2:20][C:21]1[C:30]2[N:31]=[C:32]([CH2:43][O:8][N:9]3[C:10](=[O:19])[C:11]4[C:12](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:14])[N:33]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[C:29]=2[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 67052344HCID 67052344, compound

Product 1

HCID 67052384HCID 67052384, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.340 mL, 2.41 mmol) and N-hydroxyphthalimide (0.333 g, 2.04 mmol) were added to a suspension of N-{3-[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}-2-methylpropanamide (0.670 g, 1.86 mmol) in DMF (10 mL). The reaction was allowed to stir at room temperature for 4 hours, then was concentrated under reduced pressure. The residue was triturated with methanol to afford 0.848 g of N-[3-(4-amino-2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl]-2-methylpropanamide as a tan solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-179cfc38e42b42e99d35a06108b9f9ae
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

Loading…