1-Hydroxybenzotriazole → HCID 53726585, compound

HRID 613614Notes

Reaction equation

HRID 613614 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:26]=3[N:25]=[C:24]([CH3:27])[CH:23]=[CH:22]4)[C:9]=2[Cl:28])[CH:5]=[CH:6][CH:7]=1.[CH3:29][N:30]([CH3:44])[C:31]([C:33]1[CH:43]=[CH:42][C:36]([CH:37]=[CH:38][C:39](O)=[O:40])=[CH:35][CH:34]=1)=[O:32].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[Cl:28][C:9]1[C:10]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[C:24]([CH3:27])[CH:23]=[CH:22]3)=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[N:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[CH2:2][NH:1][C:39](=[O:40])[CH:38]=[CH:37][C:36]1[CH:42]=[CH:43][C:33]([C:31](=[O:32])[N:30]([CH3:44])[CH3:29])=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10716599HCID 10716599, compoundHCID 53747642HCID 53747642, compound

Product 1

HCID 53726585HCID 53726585, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-aminomethyl-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole (100 mg) and 4-(dimethylcarbamoyl)cinnamic acid (58.5 mg) in N,N-dimethylformamide (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (55.8 mg) and 1-hydroxybenzotriazole (49.2 mg) at ambient temperature, and the mixture was allowed to stand for 18 hours. The reaction mixture was poured into water and extracted with chloroform. The separated organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=20:1, V/V) to give 1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[4-(dimethylcarbamoyl)cinnamoylaminomethyl]pyrrole (122 mg) as an amorphous powder.

Workup

  1. extractionextracted with chloroform
  2. washThe separated organic layer was washed with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=20:1, V/V)

Sources & evidence

ORD record
ord-c3a269facf834ac4806dd91ee9e7ed87
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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