Triethylamine → HCID 67041292, compound

HRID 606060Notes

Reaction equation

HRID 606060 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][CH2:11][C:12]1[N:13]([CH2:26][C:27]#[CH:28])[C:14]2[C:19]([CH3:20])=[C:18]([CH3:21])[N:17]3[N:22]=[N:23][N:24]=[C:16]3[C:15]=2[N:25]=1)[CH3:9].[OH:29][N:30]=[C:31](Cl)[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.ClN1C(=O)CCC1=O>C1COCC1>[CH2:8]([O:10][CH2:11][C:12]1[N:13]([CH2:26][C:27]2[O:29][N:30]=[C:31]([C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[CH:28]=2)[C:14]2[C:19]([CH3:20])=[C:18]([CH3:21])[N:17]3[N:22]=[N:23][N:24]=[C:16]3[C:15]=2[N:25]=1)[CH3:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chlorideHCID 86616880HCID 86616880, compound

Product 1

HCID 67041292HCID 67041292, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the presence of triethylamine (0.50 mL, 3.4 mmol), 8-(ethoxymethyl)-5,6-dimethyl-7-prop-2-ynyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridine (0.442 g, 1.55 mmol) was reacted with N-hydroxypyridine-3-carboximidoyl chloride generated from 3-pyridinecarboxyaldehyde oxime (prepared as described in Part A of Example 5, 0.38 g, 3.11 mmol) and N-chlorosuccinimide (0.42 g, 3.11 mmol) in THF (5 mL) using the method described in Part B of Example 5. After purification by flash chromatography (silica gel, elution with 95:5 dichloromethane/methanol) and trituration in diethyl ether, the product 8-(ethoxymethyl)-5,6-dimethyl-7-[(3-pyridin-3-ylisoxazol-5-yl)methyl]-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridine was obtained (0.171 g) as a white powder.

Workup

  1. customprepared
  2. customAfter purification
  3. washby flash chromatography (silica gel, elution with 95:5 dichloromethane/methanol) and trituration in diethyl ether

Sources & evidence

ORD record
ord-920beeebbb2b4ffa88e30c8d6548d9b1
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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