1-Hydroxybenzotriazole → HCID 54321652, compound

HRID 2287462Notes

Reaction equation

HRID 2287462 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:32])=[C:9]([C:28]([Cl:31])=[CH:29][CH:30]=1)[CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[C:17]2[N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)[CH3:6])=[O:4].[CH3:33][N:34]([CH3:48])[C:35]([C:37]1[CH:47]=[CH:46][C:40]([CH:41]=[CH:42][C:43](O)=[O:44])=[CH:39][CH:38]=1)=[O:36].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:32][C:8]1[C:7]([N:5]([C:3](=[O:4])[CH2:2][NH:1][C:43](=[O:44])[CH:42]=[CH:41][C:40]2[CH:46]=[CH:47][C:37]([C:35](=[O:36])[N:34]([CH3:48])[CH3:33])=[CH:38][CH:39]=2)[CH3:6])=[CH:30][CH:29]=[C:28]([Cl:31])[C:9]=1[CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[C:17]2[N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18704968HCID 18704968, compoundHCID 53747642HCID 53747642, compound

Product 1

HCID 54321652HCID 54321652, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (80 mg), 4-(dimethylcarbamoyl)cinnamic acid (41 mg) and 1-hydroxybenzotriazole (29.9 mg) in dichloromethane (0.8 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (39.1 mg) at ambient temperature, and the mixture was stirred for 3 hours at the same temperature. To the mixture was added saturated sodium bicarbonate solution, and the separated organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol, 10:1, v/v) to give 8-[2,6-dichloro-3-[N-[4-(dimethylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (104 mg) as colorless amorphous.

Workup

  1. dry with materialthe separated organic layer was dried over magnesium sulfate
  2. customevaporated in vacuo
  3. customThe residue was purified by preparative thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-478a11b30d4c495f8ef7f1bc17659f8d
Source dataset
uspto-grants-2000_07
Patent number
US06083959

Reaction notes

Loading…