1-Hydroxybenzotriazole → HCID 19603343, compound

HRID 1604553Notes

Reaction equation

HRID 1604553 reaction equation
[C:1]([C:4]1[N:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([NH:14][CH2:15][C:16]([N:18]([C:20]2[C:21]([Cl:40])=[C:22]([C:36]([Cl:39])=[CH:37][CH:38]=2)[CH2:23][O:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[C:32]([CH3:35])[CH:31]=[CH:30]3)[CH3:19])=[O:17])=[O:13])=[CH:6][CH:5]=1)([OH:3])=O.[NH2:41][C:42]1[CH:47]=[N:46][CH:45]=[CH:44][N:43]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O>[Cl:40][C:21]1[C:20]([N:18]([CH3:19])[C:16](=[O:17])[CH2:15][NH:14][C:12](=[O:13])/[CH:11]=[CH:10]/[C:7]2[CH:8]=[N:9][C:4]([C:1](=[O:3])[NH:41][C:42]3[CH:47]=[N:46][CH:45]=[CH:44][N:43]=3)=[CH:5][CH:6]=2)=[CH:38][CH:37]=[C:36]([Cl:39])[C:22]=1[CH2:23][O:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:34]=1[N:33]=[C:32]([CH3:35])[CH:31]=[CH:30]2

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 78747AminopyrazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10769547HCID 10769547, compound

Product 1

HCID 19603343HCID 19603343, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8-[3-[N-[(E)-3-(6-carboxypyridin-3-yl)-acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (100 mg), 2-aminopyrazine (19.7 mg) and N,N-dimethylformamide (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (43 mg) and 1-hydroxybenzotriazole (35 mg), and the mixture was stirred for 36 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (methylene chloride--methanol) to give 8-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(2-pyrazinylcarbamoyl)-pyridin-3-yl]acryloylglycyl]amino]benzyloxy]-2-methylquinoline (21 mg) as an amorphous powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (methylene chloride--methanol)

Sources & evidence

ORD record
ord-a549d482298649fb863281393ca0869f
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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