Dimethyl Sulfoxide → N-(5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-2-fluoro-6-(trifluoromethyl)benzenesulfonamide

HRID 2303923Notes

Reaction equation

HRID 2303923 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.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:17]=1[S:26](Cl)(=[O:28])=[O:27].N1C=CC=CC=1.CS(C)=O>C(#N)C.C(Cl)Cl>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[C:17]=1[S:26]([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:28])=[O:27]

Participants

7

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 1049Pyridine2×HCID 114468885,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amineHCID 130094272-Fluoro-6-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 11177643N-(5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-2-fluoro-6-(trifluoromethyl)benzenesulfonamideYield 46%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

2-Amino-5,8-dimethoxy(1,2,4)triazolo[1,5-c]pyrimidine (1.0 g, 5.1 mmol) was suspended in 15 mL of dry acetonitrile in a round bottom flask equipped with magnetic stirring. To this suspension was added crude 2-fluoro-6-trifluoromethylbenzenesulfonyl chloride (3.16 g, 10.2 mmol), dry pyridine (0.8 g, 10.2 mmol), dry dimethylsulfoxide (DMSO, 0.1 g, 1.3 mmol), and the flask was fitted with a CaSO4 drying tube. The reaction was monitored by HPLC analysis over a 9 day period, during which time an additional 4 equivalents of pyridine and 0.1 equivalents of DMSO were added. The dark solution was diluted with methylene chloride (300 mL), washed with 2N hydrochloric acid (2×200 mL), washed with water (2×200 mL), dried (MgSO4), filtered, and the solvent evaporated in vacuo to give a brown residue. The brown residue was triturated 5 with diethyl ether to afford the product as a tan solid: (1.0 g, 46% yield), mp 201-203° C.; Anal. Calcd for C14H11F4N5O4S: C 39.91, H 2.63, N 16.62, S 7.61; found: C 39.77, H 2.46, N 16.34, S 7.64. 1H NMR (DMSO-d6): δ8 3.85 (s, 3H), 4.05 (s, 3H), 7.58 (s, 1H), 7.73 (m, 1H), 7.88 (s, 2H), 12.85 (bs, 1H).

Workup

  1. customequipped with magnetic stirring
  2. customthe flask was fitted with a CaSO4 drying tube
  3. washwashed with 2N hydrochloric acid (2×200 mL)
  4. washwashed with water (2×200 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto give a brown residue
  9. customThe brown residue was triturated 5 with diethyl ether

Sources & evidence

ORD record
ord-551d666947b445fd8dd30e470b1dd483
Source dataset
uspto-grants-2002_08
Patent number
US06433169B1

Reaction notes

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