Triethylamine → HCID 67052377, compound

HRID 1907946Notes

Reaction equation

HRID 1907946 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]([CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:24]2[C:29]([CH3:30])=[C:28]([CH3:31])[N:27]3[N:32]=[N:33][N:34]=[C:26]3[C:25]=2[N:35]=1>CN(C=O)C>[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]([CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41](=[O:48])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:24]2[C:29]([CH3:30])=[C:28]([CH3:31])[N:27]3[N:32]=[N:33][N:34]=[C:26]3[C:25]=2[N:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 67052213HCID 67052213, compound

Product 1

HCID 67052377HCID 67052377, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Hydroxyphthalimide (2.60 g, 16.0 mmol) and triethylamine (2.20 mL, 16.0 mmol) were added to a suspension of N-{4-[8-(chloromethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}benzamide (4.70 g, 11.4 mmol) in DMF (285 mL). The reaction mixture was allowed to stir for 3 days, then was concentrated under reduced pressure to a white slurry. Methanol was added and a white solid was isolated by filtration, washed with methanol, and dried under vacuum to afford 5.70 g of N-[4-(8-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butyl]benzamide.

Workup

  1. concentrationwas concentrated under reduced pressure to a white slurry
  2. additionMethanol was added
  3. customa white solid was isolated by filtration
  4. washwashed with methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a3665abd292d4218bbe46a4e668928e7
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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