Lithium Hexamethyldisilazide → HCID 90110944, compound

HRID 1051411Notes

Reaction equation

HRID 1051411 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.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[S:29]([C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][C:40]=1[F:41])[N:37](CC1C=CC=C3C=1CN(C(OC(C)(C)C)=O)CC3)[N:36]=[CH:35]2)(=[O:31])=[O:30]>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:29]([C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][C:40]=1[F:41])[NH:37][N:36]=[CH:35]2)(=[O:30])=[O:31]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 57732216N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amineHCID 90111881HCID 90111881, compound

Product 1

HCID 90110944HCID 90110944, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine (1.6 g, 6.39 mmol, 1.5 equiv) in THF (32.0 mL) at −78° C. was added LHMDS (10.65 mL, 10.65 mmol, 2.5 equiv) and the system was stirred for 30 min followed by the slow addition of 6-fluoro-1H-indazole-5-sulfonyl chloride (1-4, 1.0 g, 4.26 mmol, 1.0 equiv) in THF (10.65 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 and used directly in the next step.

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

Sources & evidence

ORD record
ord-ad133f1faf534f8d9dae3962d7f181b3
Source dataset
uspto-grants-2016_07
Patent number
US09388179B2

Reaction notes

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