1-Hydroxybenzotriazole → HCID 23090104, compound

HRID 1437221Notes

Reaction equation

HRID 1437221 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]([OH:22])=O)=[N:10]2)=[CH:5][CH:4]=1.[N:23]([CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]1)=[N+:24]=[N-:25].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:12][C:11]([C:20]([N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH:28]3[CH2:27][CH2:26][N:23]=[N+:24]=[N-:25])=[O:22])=[N:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23090125HCID 23090125, compoundHCID 23090164HCID 23090164, compound

Product 1

HCID 23090104HCID 23090104, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-(6-Methoxy-3-pyridyl)-5-phenylpyrazole-3-carboxylic acid (191 mg) obtained from Referential Example 41, 2-(2-azidoethyl)piperidine (100 mg) obtained from Referential Example 80, 1-hydroxybenzotriazole (88 mg), and triethylamine (316 μL) were dissolved in methylene chloride (10 mL). To the resultant mixture, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (186 mg) was added at room temperature, followed by stirring for 14 hours. The residue obtained by removal through evaporation of the reaction solvent under reduced pressure was partitioned between water and ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The residue obtained by removal through evaporation of the solvent under reduced pressure was purified through silica gel thin-layer chromatography (hexane-ethyl acetate), to thereby give the title compound as an oily product (227 mg, 81%).

Workup

  1. customThe residue obtained by removal through evaporation of the reaction solvent under reduced pressure
  2. customwas partitioned between water and ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe residue obtained by removal through evaporation of the solvent under reduced pressure
  7. customwas purified through silica gel thin-layer chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f3fc414b95f44264b319c77ecd9b7a92
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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