1-Hydroxybenzotriazole → HCID 86701369, compound

HRID 570985Notes

Reaction equation

HRID 570985 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[S:7])=[CH:4][C:3]=1[C:11]#[C:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[Cl:45][C:46]1[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[C:47]=1[C:48]([NH:50][NH2:51])=[O:49]>CN(C)C=O>[Cl:45][C:46]1[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[C:47]=1[C:48]([N:50]([C:6](=[S:7])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]#[C:12][C:13]2[CH:14]=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:4]=1)[NH2:51])=[O:49]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69019186HCID 69019186, compoundHCID 178425914HCID 178425914, compound

Product 1

HCID 86701369HCID 86701369, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methyl-3-[(quinolin-3-yl)ethynyl]thiobenzoic acid (0.15 g, 0.5 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.15 g, 0.7 mmol) and 1-hydroxybenzotriazole (0.1 g, 0.7 mmol) in N,N-dimethylformamide (15 ml) was stirred at ambient temperature for 1 hr. 2-Chloro-6-methylbenzohydrazide (0.125 g, 0.5 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 finally purified by flash chromatography on silica gel (elution with 10% methanol in dichloromethane) to get 2-chloro-6-methyl-N-[4-methyl-3-[2-(3-quinolyl)ethynyl]thiobenzoyl]benzohydrazide 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. customfinally purified by flash chromatography on silica gel (elution with 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9bc23a12139f441295c7ae2076a61f83
Source dataset
uspto-grants-2015_05
Patent number
US09024021B2

Reaction notes

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