Water → HCID 22563219, compound

HRID 982714Notes

Reaction equation

HRID 982714 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:25][C:24]([CH2:26]O)=[CH:23][C:13]=3[N:14]([CH2:16][C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS([Cl:44])(=O)=O.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:28])[C:12]3[S:25][C:24]([CH2:26][Cl:44])=[CH:23][C:13]=3[N:14]([CH2:16][C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])[CH:15]=2)=[O:9])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 22563215N-(4-chlorobenzyl)-2-(hydroxymethyl)-4-{2-[methoxy(methyl)amino]-2-oxoethyl}-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 22563219HCID 22563219, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(4-chlorobenzyl)-2-(hydroxymethyl)-4-{2-[methoxy(methyl)amino]-2-oxoethyl}-7-oxo-4,7-dihydrothieno [3,2-b]pyridine-6-carboxamide (80 mg, 0.18 mmol), collidine (59 μL, 0.44 mmol) and DMAP (3.2 mg) in DMF (2.6 mL) was added methanesulfonyl chloride (35 μL, 0.44 mmol). The reaction was stirred at room temperature for 24 hrs, then cooled to 0° C. before the addition of water (5 mL). The resulting ppt was collected by filtration and washed with water and dried in vacuo, leaving the title compound as an off-white solid (80 mg). The title compound is also a compound of formula I.

Workup

  1. filtrationThe resulting ppt was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ac5a25c1784e408195cc460a0be4a7b0
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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