Pyridine → N-[(3-{4-[(Acetylamino)methyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]-5-chloro-2-thiophenecarboxamide

HRID 68474

Reaction equation

HRID 68474 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH:12]([CH2:14][NH:15][C:16]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[O:17])[O:11][C:10]2=[O:24])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].CCOCC>C1COCC1.ClCCl>[C:31]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH:12]([CH2:14][NH:15][C:16]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[O:17])[O:11][C:10]2=[O:24])=[CH:5][CH:4]=1)(=[O:33])[CH3:32]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 21070786N-({3-[4-(aminomethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-5-chloro-2-thiophenecarboxamide

Product 1

HCID 21070779N-[(3-{4-[(Acetylamino)methyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]-5-chloro-2-thiophenecarboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., a mixture of 30 mg (0.082 mmol) of N-({3-[4-(aminomethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-5-chloro-2-thiophene-carboxamide (from Example 148) in 1.5 ml of absolute THF and 1.0 ml of absolute dichloromethane, and 0.02 ml of absolute pyridine is mixed with acetic anhydride (0.015 ml, 0.164 mmol). The mixture is stirred at room temperature overnight. Addition of ether and crystallization affords the product. Yield: 30 mg (87% of theory),

Workup

  1. customaffords the product

Sources & evidence

ORD record
ord-ec868296347c4d758c0de2e86b86d396
Source dataset
uspto-grants-2014_09
Patent number
US08822458B2

Linked notes

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