Water → 4-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(chloromethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23624Notes

Reaction equation

HRID 23624 reaction equation
[NH2:1][C:2](=[O:28])[CH2:3][N:4]1[CH:9]=[C:8]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:21])[C:6]2[S:22][C:23]([CH2:26]O)=[C:24]([CH3:25])[C:5]1=2.N1C(C)=CC(C)=CC=1C.CS([Cl:42])(=O)=O.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:1][C:2](=[O:28])[CH2:3][N:4]1[CH:9]=[C:8]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:21])[C:6]2[S:22][C:23]([CH2:26][Cl:42])=[C:24]([CH3:25])[C:5]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 225743684-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 225743174-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(chloromethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 101.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (58 mg, 0.13 mmol), collidine (44 μL, 0.33 mmol) and DMAP (2.4 mg) in DMF (2.25 mL) was added methanesulfonyl chloride (26 μL, 0.33 mmol). The mixture was stirred at room temperature for 48 hrs. Additional reagents (half original amounts) were added and the reaction was stirred another 4 hrs. The reaction was chilled in ice before the addition of water (8 mL). The ppt was collected by filtration, washed with water and dried in vacuo, giving the title compound as a white solid (58 mg).

Workup

  1. additionAdditional reagents (half original amounts) were added
  2. stirringthe reaction was stirred another 4 hrs
  3. filtrationThe ppt was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d1af47fdf755424481fe79f7a1a8e283
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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