Sodium Hydroxide → HCID 59311529, compound

HRID 1693275Notes

Reaction equation

HRID 1693275 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[C:5]2[C:14]3[C:8]([CH2:9][CH:10]([C:15]([OH:17])=O)[S:11][C:12]=3[N:13]=1)=[N:7][N:6]2[CH2:18][C:19]1[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([CH3:28])=[CH:21][N:20]=1.Cl.CN.O.O[N:34]1[C:38]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CN(C)C=O>[NH2:2][C:3]1[N:4]=[C:5]2[C:14]3[C:8]([CH2:9][CH:10]([C:15]([NH:34][CH3:38])=[O:17])[S:11][C:12]=3[N:13]=1)=[N:7][N:6]2[CH2:18][C:19]1[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([CH3:28])=[CH:21][N:20]=1

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 67280128HCID 67280128, compound

Product 1

HCID 59311529HCID 59311529, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture composed of 4-amino-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxylic acid hydrochloride of Example 8 (42 mg), methylamine hydrochloride (13 mg), 1-hydroxybenzotriazole monohydrate (14 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35 mg), diisopropylethylamine (79 μL) and dehydrated N,N-dimethylformamide (1 mL) was stirred at room temperature for 48 hours. A 0.5 N sodium hydroxide solution was added to the reaction mixture, and the solid was collected by filtration. The solid collected by filtration was dissolved in a mixed solvent of chloroform-methanol, followed by purification by silica gel thin-layer chromatography (chloroform-methanol) to obtain the title compound (17.9 mg, 49%) as a solid.

Workup

  1. filtrationthe solid was collected by filtration
  2. filtrationThe solid collected by filtration
  3. dissolutionwas dissolved in a mixed solvent of chloroform-methanol
  4. customfollowed by purification by silica gel thin-layer chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-e588102d00674b58b25c887b4ca652d4
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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