1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-cyclopropyl-3-ethoxy-N-[(2-iodo-6-methoxyphenyl)sulfonyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide

HRID 2264127Notes

Reaction equation

HRID 2264127 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].[CH:14]1([N:17]2[C:21](=[O:22])[N:20]([C:23](OC3C=CC=CC=3)=[O:24])[N:19]=[C:18]2[O:32][CH2:33][CH3:34])[CH2:16][CH2:15]1.N12CCCN=C1CCCCC2>C(#N)C>[CH:14]1([N:17]2[C:21](=[O:22])[N:20]([C:23]([NH:13][S:10]([C:3]3[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=3[I:1])(=[O:12])=[O:11])=[O:24])[N:19]=[C:18]2[O:32][CH2:33][CH3:34])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 120566244-cyclopropyl-3-ethoxy-5-oxo-1-phenyloxycarbonyl-4,5-dihydro-1H-1,2,4-triazoleHCID 231507892-Iodo-6-methoxybenzenesulfonamide

Product 1

HCID 119477864-cyclopropyl-3-ethoxy-N-[(2-iodo-6-methoxyphenyl)sulfonyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 250 mg (0.80 mmol) of 2-iodo-6-methoxybenzenesulfonamide in 3 ml of acetonitrile is admixed at room temperature first with 254.08 mg (0.88 mmol) of 4-cyclopropyl-3-ethoxy-5-oxo-1-phenyloxycarbonyl-4,5-dihydro-1H-1,2,4-triazole and then slowly with 0.24 ml (1.60 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. After 60 min of stirring at room temperature the solution is adjusted slowly to a pH of 1 using 2 N salt solution. The precipitated solid is filtered off with suction, washed with diisopropyl ether and acetonitrile, and dried. This gives 267 mg (62% of theory) of 4-cyclopropyl-3-ethoxy-N-[(2-iodo-6-methoxyphenyl)sulfonyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide.

Workup

  1. filtrationThe precipitated solid is filtered off with suction
  2. washwashed with diisopropyl ether and acetonitrile
  3. customdried

Sources & evidence

ORD record
ord-43ac85e9da854e32b5599505e3beb8a2
Source dataset
uspto-grants-2010_12
Patent number
US07855166B2

Reaction notes

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