Dimethylformamide → N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(1,3-dimethylpyrazol-5-yl)urea

HRID 396287Notes

Reaction equation

HRID 396287 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([Cl:8])=[CH:6][CH:7]=1.N(C([C:19]1[N:23]([CH3:24])[N:22]=[C:21]([CH3:25])[CH:20]=1)=O)=[N+]=[N-].C[N:27](C)[CH:28]=[O:29]>>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:28]([NH:27][C:19]2[N:23]([CH3:24])[N:22]=[C:21]([CH3:25])[CH:20]=2)=[O:29])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamideHCID 230036335-(Azidocarbonyl)-1,3-dimethylpyrazole

Product 1

HCID 10291982N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(1,3-dimethylpyrazol-5-yl)ureaYield 7.7%

Procedure

Under Ar, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (137 mg, 0.61 mmol) and 5-(azidocarbonyl)-1,3-dimethylpyrazole (203 mg, 1.23 mmol) in 2 mL of N,N-dimethyl-formamide was stirred at room temperature for 3 days. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (17 mg, 7.7%). LC-MS (m/z) 360.2 (M+).

Workup

  1. customPurification upon Gilson HPLC
  2. washeluting with acetonitrile/water (10/90, v/v to 90/10

Sources & evidence

ORD record
ord-8f0d5a4500af4d2585f402c7648e3d19
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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