Triethylamine → HCID 178454363, compound

HRID 1807201Notes

Reaction equation

HRID 1807201 reaction equation
Cl.CO[C:4](=[NH:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[C:15]([O:19][C:20]([NH:22][NH2:23])=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>C(O)C>[C:15]([O:19][C:20]([NH:22][NH:23][C:4](=[NH:14])[C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 12410479HCID 12410479, compound

Product 1

HCID 178454363HCID 178454363, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4-nitro-benzimidic acid methyl ester hydrochloride (500 mg, 2.31 mmol) in ethanol (8 mL), hydrazinecarboxylic acid tert-butyl ester (305 mg, 2.31 mmol) was added followed by triethylamine. The mixture was stirred at rt over night. The solvent was removed and the residue was suspended in methylene chloride (10 mL). The mixture was filtered and the filtrate was concentrated to about 4 mL and loaded on a 20 g silica gel column. Eluting with 40-90% EtOAc/Hexanes on an ISCO machine gave a yellow solid. 410 mg. Which was directly used for the next step.

Workup

  1. customThe solvent was removed
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to about 4 mL
  4. washEluting with 40-90% EtOAc/Hexanes on an ISCO machine
  5. customgave a yellow solid

Sources & evidence

ORD record
ord-dc7db70e9e7949afa958b23766879ae7
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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