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

HRID 1091415Notes

Reaction equation

HRID 1091415 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-5704b7ccd9a446f0a54a1232870cda32
Source dataset
uspto-grants-2012_03
Patent number
US08129378B2

Reaction notes

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