Dimethylformamide → HCID 9902771, compound

HRID 396288Notes

Reaction equation

HRID 396288 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]=[CH:21][CH:20]=1)=O)=[N+]=[N-].C[N:26](C)[CH:27]=[O:28]>>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:27]([NH:26][C:19]2[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=2)=[O:28])[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 23003632HCID 23003632, compound

Product 1

HCID 9902771HCID 9902771, compoundYield 7.7%

Procedure

Under Ar, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (100 mg, 0.45 mmol) and 5-(azidocarbonyl)-1-methylpyrazol (280 mg, 1.85 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 (12 mg, 7.7%). LC-MS (m/z) 346.0 (M+).

Workup

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

Sources & evidence

ORD record
ord-58c98011528c425ea086747883f58c8f
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

Loading…