4-Aminopyridine → HCID 21254834, compound

HRID 636527Notes

Reaction equation

HRID 636527 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:41])=[C:22]([C:37]([Cl:40])=[CH:38][CH:39]=2)[CH2:23][O:24][C:25]2[C:33]3[N:32]=[C:31]([O:34][CH3:35])[N:30]([CH3:36])[C:29]=3[CH:28]=[CH:27][CH:26]=2)[CH3:19])=[O:17])=[O:13])=[CH:6][CH:5]=1)([OH:3])=O.[NH2:42][C:43]1[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[Cl:41][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:42][C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)=[CH:5][CH:6]=2)=[CH:39][CH:38]=[C:37]([Cl:40])[C:22]=1[CH2:23][O:24][C:25]1[C:33]2[N:32]=[C:31]([O:34][CH3:35])[N:30]([CH3:36])[C:29]=2[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21254645HCID 21254645, compound

Product 1

HCID 21254834HCID 21254834, compoundYield 7.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-[3-[N-[(E)-3-(6-carboxypyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (90 mg) and 4-aminopyridine (14.3 mg) in N,N-dimethylformamide (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (31.7 mg) and 1-hydroxybenzotriazole (26.4 mg) at ambient temperature, and after standing for 1 day, the mixture was stirred for 8 hours at 50° C. To the mixture was added water, and extracted with ethyl acetate. The extract was washed with 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, 12:1, v/v) to give 4-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(4-pyridylcarbamoyl)pyridin-3-yl]acryloylglycyl]amino]-benzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (7.8 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 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

Sources & evidence

ORD record
ord-b0ebf7fe76354760b2c3a09042b3c9c1
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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