Triethylamine → HCID 86627647, compound

HRID 1907935Notes

Reaction equation

HRID 1907935 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].[C:20]([O:24][C:25](=[O:46])[NH:26][CH2:27][CH2:28][CH2:29][N:30]1[C:42]2[C:41]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[N:35]=[C:34]([NH2:43])[C:33]=2[N:32]=[C:31]1[CH2:44]Cl)([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.O>[NH2:43][C:34]1[C:33]2[N:32]=[C:31]([CH2:44][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:30]([CH2:29][CH2:28][CH2:27][NH:26][C:25](=[O:46])[O:24][C:20]([CH3:21])([CH3:23])[CH3:22])[C:42]=2[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[N:35]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 86627648HCID 86627648, compound

Product 1

HCID 86627647HCID 86627647, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Triethylamine (4.6 mL, 33.1 mmol) was added to a solution of N-hydroxyphthalimide (2.16 g, 13.2 mmol) in DMF (10 mL). A solution of tert-butyl[3-(4-amino-2-chloromethyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]carbamate (4.3 g, 11.0 mmol) in DMF (20 ml) was added. The reaction was stirred at ambient temperature for 3.5 hours and then diluted with water (100 mL). The resulting precipitate was isolated by filtration, washed with water, and then dried in a vacuum oven at 60° C. over the weekend to provide 4.25 g of tert-butyl (3-{4-amino-2-[(1,3-dioxo-1,3-dihydroisoindol-2-yl)oxymethyl]-1H-imidazo[4,5-c]quinolin-1-yl}propyl)carbamate as a light yellow solid.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. washwashed with water
  3. customdried in a vacuum oven at 60° C. over the weekend

Sources & evidence

ORD record
ord-56099b492cd1428a8949818ef3083016
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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