1-Hydroxybenzotriazole → benzyl N'-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbonyl]hydrazinecarboxylate

HRID 406324Notes

Reaction equation

HRID 406324 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[NH:2][NH2:3].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:35][O:36][C:37]1[N:42]=[C:41]([C:43](O)=[O:44])[CH:40]=[CH:39][C:38]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:35][O:36][C:37]1[N:42]=[C:41]([C:43]([NH:3][NH:2][C:1]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[O:44])[CH:40]=[CH:39][C:38]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1

Participants

9

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666084476-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylic acid

Product 1

HCID 66608695benzyl N'-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbonyl]hydrazinecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl carbazate (27.8 g), 1-hydroxybenztriazole (24.8 g) and 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (35.4 g) were sequentially added to a solution of 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylic acid obtained in Preparation Example 1-5 (51.9 g) and IPEA (44 mL) in N,N-dimethylformamide (184 mL), and the mixture was stirred at room temperature for six hours and 30 minutes. Ethyl acetate, ice water and a saturated sodium bicarbonate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then filtered through an NH silica gel pad. The resulting filtrate was concentrated under reduced pressure. Ethyl acetate was added to the resulting residue, and the powder was collected by filtration. The resulting powder was air-dried to obtain 28.4 g of the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered through an NH silica gel pad
  4. concentrationThe resulting filtrate was concentrated under reduced pressure
  5. additionEthyl acetate was added to the resulting residue
  6. filtrationthe powder was collected by filtration
  7. customThe resulting powder was air-dried

Sources & evidence

ORD record
ord-e231955b52be4b60b5f92233b1492f01
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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