N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine → HCID 90110743, compound

HRID 1051409Notes

Reaction equation

HRID 1051409 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][NH:6][C:7]1[S:11][N:10]=[CH:9][N:8]=1.[F:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[N:24][N:25]2[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[I:35])=[CH:21][C:20]=1[S:36](Cl)(=[O:38])=[O:37]>C1COCC1>[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]([C:7]1[S:11][N:10]=[CH:9][N:8]=1)[S:36]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:19]=1[F:18])[N:25]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[I:35])[N:24]=[CH:23]2)(=[O:37])=[O:38]

Participants

4

Reactant 2

HCID 57732216N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amineHCID 90109250HCID 90109250, compound

Product 1

HCID 90110743HCID 90110743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine (0.61 g, 2.44 mmol, 1.1 equiv) in THF (5.55 mL) at −78° C. was added LIHMDS (2.441 mL, 2.44 mmol, 1.1 equiv) and stirred for 0.5 h followed by the slow addition of 6-fluoro-1-(2-iodobenzyl)-1H-indazole-5-sulfonyl chloride (2-2, 1.0 g, 2.22 mmol, 1.0 equiv) in THF (1.85 mL) and stirred overnight as the system approached ambient temperature. The reaction was quenched with ammonium chloride and extracted with EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated and the residue was purified by normal phase chromatography (0→40% EtOAc in hexanes). ESI+ MS [M+H]+ C25H21FIN5O4S2: 666.1 found, 666.5 required.

Workup

  1. stirringstirred overnight as the system
  2. customapproached ambient temperature
  3. customThe reaction was quenched with ammonium chloride
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by normal phase chromatography (0→40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4f36c29efc804378bfb9b259b4150a03
Source dataset
uspto-grants-2016_07
Patent number
US09388179B2

Reaction notes

Loading…