Furosemide → Cyanomethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate

HRID 1676929Notes

Reaction equation

HRID 1676929 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:10]([Cl:21])[CH:9]=2)[O:4][CH:5]=1.Cl[CH2:23][C:24]#[N:25]>CN(C=O)C>[NH2:20][S:17]([C:11]1[C:10]([Cl:21])=[CH:9][C:8]([NH:7][CH2:6][C:3]2[O:4][CH:5]=[CH:1][CH:2]=2)=[C:13]([CH:12]=1)[C:14]([O:16][CH2:23][C:24]#[N:25])=[O:15])(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 3440FurosemideHCID 7856Chloroacetonitrile

Product 1

HCID 11682180Cyanomethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 2, furosemide can be reacted with chloroacetonitrile in DMF to yield cyanomethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]-benzoate.

Sources & evidence

ORD record
ord-470e984fcb0749cda017bbec87502a67
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

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