1-Hydroxybenzotriazole → 8-[2,6-dichloro-3-[N-[3-[N-(3-methylcarbamoylphenyl)carbamoyl]propionyl]-N-methylamino]benzyloxy]-2-methylquinoline

HRID 1604601Notes

Reaction equation

HRID 1604601 reaction equation
[C:1]([CH2:4][CH2:5][C:6]([N:8]([C:10]1[C:11]([Cl:30])=[C:12]([C:26]([Cl:29])=[CH:27][CH:28]=1)[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[C:22]([CH3:25])[CH:21]=[CH:20]2)[CH3:9])=[O:7])([OH:3])=O.[NH2:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([NH:37][CH3:38])=[O:36].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:30][C:11]1[C:10]([N:8]([C:6](=[O:7])[CH2:5][CH2:4][C:1](=[O:3])[NH:31][C:32]2[CH:41]=[CH:40][CH:39]=[C:34]([C:35](=[O:36])[NH:37][CH3:38])[CH:33]=2)[CH3:9])=[CH:28][CH:27]=[C:26]([Cl:29])[C:12]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[C:22]([CH3:25])[CH:21]=[CH:20]2

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 6765263-Amino-N-methylbenzamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19603338HCID 19603338, compound

Product 1

HCID 196033938-[2,6-dichloro-3-[N-[3-[N-(3-methylcarbamoylphenyl)carbamoyl]propionyl]-N-methylamino]benzyloxy]-2-methylquinolineYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to amixture of 8-[3-[N-(3-carboxypropionyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (139 mg), 3-amino-N-methylbenzamide (51.3 mg) and anhydrous dichloromethane (4 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (71.5 mg) and 1-hydroxybenzotriazole (54.6 mg). The mixture was stirred for 12 hours at ambient temperature ans washed with water. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purifed by preparative thin-layer chromatography (chloroform-methanol) followed by pulverization with diethyl ether to give 8-[2,6-dichloro-3-[N-[3-[N-(3-methylcarbamoylphenyl)carbamoyl]propionyl]-N-methylamino]benzyloxy]-2-methylquinoline (103 mg) as an amorphous powder.

Workup

  1. washans washed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-7c427f62e5f242f7b3fd6a92bfe762b8
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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