3-Amino-5-chlorothiophene-2-sulfonamide → 5-Hydroxy-2-(3-methyl-butyl)-3-oxo-6-thiophen-2-yl-2,3-dihydro-pyridazine-4-carboxylic acid (5-chloro-2-sulfamoyl-thiophen-3-yl)-amide

HRID 30979Notes

Reaction equation

HRID 30979 reaction equation
C(O[C:4]([C:6]1[C:7](=[O:23])[N:8]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[N:9]=[C:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[C:11]=1[OH:12])=[O:5])C.[NH2:24][C:25]1[CH:29]=[C:28]([Cl:30])[S:27][C:26]=1[S:31]([NH2:34])(=[O:33])=[O:32]>>[Cl:30][C:28]1[S:27][C:26]([S:31](=[O:33])(=[O:32])[NH2:34])=[C:25]([NH:24][C:4]([C:6]2[C:7](=[O:23])[N:8]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[N:9]=[C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:11]=2[OH:12])=[O:5])[CH:29]=1

Participants

3

Reactant 2

HCID 109559343-Amino-5-chlorothiophene-2-sulfonamideHCID 597914415-Hydroxy-2-(3-methyl-butyl)-3-oxo-6-thiophen-2-yl-2,3-dihydro-pyridazine-4-carboxylic acid ethyl ester

Product 1

HCID 586938565-Hydroxy-2-(3-methyl-butyl)-3-oxo-6-thiophen-2-yl-2,3-dihydro-pyridazine-4-carboxylic acid (5-chloro-2-sulfamoyl-thiophen-3-yl)-amide

Conditions

Temperature
160 °C

Procedure

The ester (13a) made by Method 4 (86 mg, 0.26 mmol) and 3-Amino-5-chloro-thiophene-2-sulfonic acid amide (14b) (54 mg, 0.26 mmol) were mixed in a reaction vial and stirred in a preheated oil-bath at 160° C. for 10 mins to give the corresponding 5-hydroxy-2-(3-methyl-butyl)-3-oxo-6-thiophen-2-yl-2,3-dihydro-pyridazine-4-carboxylic acid (5-chloro-2-sulfamoyl-thiophen-3-yl)-amide (15a) as a dark yellow solid which was used directly in next step without further purification. LC-MS (ESI+): m/e=503.09 [M+1]+(exact ms: 502.02).

Workup

  1. additionwere mixed in a reaction vial

Sources & evidence

ORD record
ord-984afd7ee4bb47b89a41c2a5659fbde4
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

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