2-Pyrazinecarboxylic acid → HCID 19603250, compound

HRID 1604552Notes

Reaction equation

HRID 1604552 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][CH2:13][C:14]([N:16]([C:18]2[C:19]([Cl:38])=[C:20]([C:34]([Cl:37])=[CH:35][CH:36]=2)[CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[C:27]3[C:32]=2[N:31]=[C:30]([CH3:33])[CH:29]=[CH:28]3)[CH3:17])=[O:15])=[O:11])=[CH:4][CH:3]=1.[N:39]1[CH:44]=[CH:43][N:42]=[CH:41][C:40]=1[C:45](O)=[O:46].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:38][C:19]1[C:18]([N:16]([CH3:17])[C:14](=[O:15])[CH2:13][NH:12][C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]2[CH:6]=[N:7][C:2]([NH:1][C:45]([C:40]3[CH:41]=[N:42][CH:43]=[CH:44][N:39]=3)=[O:46])=[CH:3][CH:4]=2)=[CH:36][CH:35]=[C:34]([Cl:37])[C:20]=1[CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[C:30]([CH3:33])[CH:29]=[CH:28]2

Participants

7

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10816486HCID 10816486, compound

Product 1

HCID 19603250HCID 19603250, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8-[3-[N-[(E)-3-(6-aminopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (90.0 mg), 2-pyrazinecarboxylic acid (24.3 mg) and dimethylformamide (0.9 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (43.9 mg) and 1-hydroxybenzotriazole (35.4 mg). After being stirred for 37 hours at ambient temperature, the mixture was poured into saturated sodium bicarbonate solution and extracted with chloroform. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform--methanol) to give 8-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(2-pyrazinecarboxamido)-pyridin-3-yl]acryloylglycyl]amino]benzyloxy]-2-methylquinoline (43.7 mg) as a solid.

Workup

  1. extractionextracted with chloroform
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin-layer chromatography (chloroform--methanol)

Sources & evidence

ORD record
ord-c9bda33bc26e4c73be65f4533544014d
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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