1-Hydroxybenzotriazole → HCID 59053813, compound

HRID 570984Notes

Reaction equation

HRID 570984 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][C:13]2[N:18]=[C:17]([C:19]([OH:21])=O)[CH:16]=[CH:15][CH:14]=2)[CH:2]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[Cl:44][C:45]1[CH:54]=[CH:53][CH:52]=[C:51]([CH3:55])[C:46]=1[C:47]([NH:49][NH2:50])=[O:48]>CN(C)C=O>[Cl:44][C:45]1[CH:54]=[CH:53][CH:52]=[C:51]([CH3:55])[C:46]=1[C:47]([NH:49][NH:50][C:19]([C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([C:12]#[C:11][C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:18]=1)=[O:21])=[O:48]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69019186HCID 69019186, compoundHCID 70557114HCID 70557114, compound

Product 1

HCID 59053813HCID 59053813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-[(quinolin-3-yl)ethynyl]pyridine-2-carboxylic acid (0.05 g, 0.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.04 g, 0.2 mmol) and 1-hydroxybenzotriazole (0.03 g, 0.2 mmol) in N,N-dimethylformamide (10 ml) was stirred at ambient temperature for 1 hr. 2-chloro-6-methylbenzohydrazide (0.03 g, 0.2 mmol) was added and the mixture stirred for 12 hrs at ambient temperature. Concentration and trituration of the residue with water produced a solid which was filtered, washed with water and dried in vacuo. Leaching the product with methanol and drying in vacuo gave N′-(2-Chloro-6-methylbenzoyl)-6-[2-(3-quinolyl)ethynyl]pyridine-2-carboxylic acid hydrazide as a white solid.

Workup

  1. stirringthe mixture stirred for 12 hrs at ambient temperature
  2. concentrationConcentration and trituration of the residue with water
  3. customproduced a solid which
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried in vacuo
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-7a10c4d9b8444f548fd9f1a15b963255
Source dataset
uspto-grants-2015_05
Patent number
US09024021B2

Reaction notes

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