HCID 10357758, compound → HCID 136355278, compound

HRID 601397Notes

Reaction equation

HRID 601397 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[C:10](=[C:15](SC)SC)[C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][C:23]=1[S:33]([NH2:36])(=[O:35])=[O:34]>O1CCOCC1>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]2[NH:21][C:22]3[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])=[CH:24][C:23]=3[S:33](=[O:35])(=[O:34])[N:36]=2)[C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10357758HCID 10357758, compoundHCID 249506572-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

Product 1

HCID 136355278HCID 136355278, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the product of Example 426B (0.028 g, 0.092 mmol) and the product of Example 425D (0.025 g, 0.092 mmol) in 1,4-dioxane was heated at 100° C. for 40 minutes. The solvent was removed under a stream of with warm nitrogen and the residue was triturated with water and ethyl acetate. The precipitate in the organic layer was filtered and dried to yield the title compound (0.006 g, 12%). MS (ESI−) m/z 473 (M−H)−. 1H NMR (500 MHz, DMSO-D6) δ 3.06 (s, 3 H) 5.21 (s, 2 H) 6.38 (d, J=4.88 Hz, 1 H) 7.34 (m, 5 H) 7.55 (m, 3 H) 8.18 (d, J=3.05 Hz, 1 H) 10.25 (s, 1 H) 13.87 (s, 1 H) 14.05 (s, 1 H).

Workup

  1. customThe solvent was removed under a stream of with warm nitrogen
  2. customthe residue was triturated with water and ethyl acetate
  3. filtrationThe precipitate in the organic layer was filtered
  4. customdried

Sources & evidence

ORD record
ord-078111c1e338437eaad2308925d11b0d
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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