Triethylamine → HCID 67052465, compound

HRID 599413Notes

Reaction equation

HRID 599413 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].Cl[CH2:14][C:15]1[N:16]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:17]2[C:22]([CH3:23])=[C:21]([CH3:24])[N:20]3[N:25]=[N:26][N:27]=[C:19]3[C:18]=2[N:28]=1.C(N(CC)CC)C>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][CH2:14][C:15]1[N:16]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:17]2[C:22]([CH3:23])=[C:21]([CH3:24])[N:20]3[N:25]=[N:26][N:27]=[C:19]3[C:18]=2[N:28]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 10665N-Hydroxyphthalimide2×HCID 67052387HCID 67052387, compound

Product 1

HCID 67052465HCID 67052465, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Hydroxyphthalimide (64 mg, 0.39 mmol) was added to a stirred solution of N-{4-[8-(chloromethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}methanesulfonamide (100 mg, 0.26 mmol) in DMF (2.6 mL). Triethylamine (0.109 mL, 0.78 mmol) was added dropwise, causing the solution to turn red. After 3 hours, more N-hydroxyphthalimide and triethylamine (3 equivalents each) were added and stirring was continued overnight. The solvent was removed under reduced pressure. To the resulting oil was added ethyl acetate and water, which caused a yellow solid to form. The solid was isolated by filtration, washed with chloroform, and then was triturated with ethyl acetate and isolated by filtration to afford 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]methanesulfonamide as a yellow solid.

Workup

  1. waitwas continued overnight
  2. customThe solvent was removed under reduced pressure
  3. additionTo the resulting oil was added ethyl acetate and water, which
  4. customto form
  5. customThe solid was isolated by filtration
  6. washwashed with chloroform
  7. customwas triturated with ethyl acetate
  8. customisolated by filtration

Sources & evidence

ORD record
ord-7ed2850947c5478c9d49f45042661019
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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