Dimethyl Sulfoxide → 3-Methoxy-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)thiophene-2-sulfonamide

HRID 1058557Notes

Reaction equation

HRID 1058557 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1.[CH3:15][O:16][C:17]1[CH:21]=[CH:20][S:19][C:18]=1[S:22](Cl)(=[O:24])=[O:23].N1C=CC=CC=1.CS(C)=O>C(#N)C>[CH3:15][O:16][C:17]1[CH:21]=[CH:20][S:19][C:18]=1[S:22]([NH:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 112988223-methoxythiophene-2-sulfonyl ChlorideHCID 114468885,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

Product 1

HCID 111645993-Methoxy-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)thiophene-2-sulfonamideYield 50.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of 0.8 g (4.5 mmol) of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine in 7 mL of acetonitrile was added 1.3 g (6.1 mmol) of 3-methoxythiophene-2-sulfonylchloride, 0.6 mL of dry pyridine and 0.003 mL of dry DMSO. After 96 hr, the reaction mixture was partitioned with CH2Cl2 and water. The organic phase was separated, washed with dilute aqueous HCl, dried over MgSO4, filtered and concentrated. The residue was taken into a small amount of CH2Cl2 before ether was added slowly with stirring to precipitate a fine tan solid. The solid was collected by filtration and dried under vacuum to give 0.85 g (50%) of the desired product. mp 227-228° C. 1H NMR (300 MHz, DMSO-d6): δ 12.1 (s, 1H); 7.8 (d, 1H, J=5.6); 7.6 (s, 1H); 7.0 (d, 1H, J=5.6); 4.1 (s, 3H); 3.9 (s, 3H); 3.8 (s, 3H). Calc'd for C12H13N5O5S2: C, 38.81; H, 3.53; N, 18.86; S, 17.27. Found: C, 38.32; H, 3.49; N, 18.91; S, 17.34.

Workup

  1. customthe reaction mixture was partitioned with CH2Cl2 and water
  2. customThe organic phase was separated
  3. washwashed with dilute aqueous HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionwas added slowly
  8. customto precipitate a fine tan solid
  9. filtrationThe solid was collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-12656019d2704e9780f5e544579e0224
Source dataset
uspto-grants-2003_02
Patent number
US06518222B2

Reaction notes

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