Lithium Hexamethyldisilazide → N-(2,4-dimethoxybenzyl)-2,4-difluoro-5-methyl-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 337935Notes

Reaction equation

HRID 337935 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:8][CH:9]=[N:10][N:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:28][C:29]1[CH:34]=[C:33]([F:35])[C:32]([CH3:36])=[CH:31][C:30]=1[S:37](Cl)(=[O:39])=[O:38]>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:8][CH:9]=[N:10][N:11]=1)[S:37]([C:30]1[CH:31]=[C:32]([CH3:36])[C:33]([F:35])=[CH:34][C:29]=1[F:28])(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 58042278N-(2,4-dimethoxybenzyl)-1,3,4-thiadiazol-2-amineHCID 594365302,4-Difluoro-5-methylbenzenesulfonyl chloride

Product 1

HCID 59436572N-(2,4-dimethoxybenzyl)-2,4-difluoro-5-methyl-N-1,3,4-thiadiazol-2-ylbenzenesulfonamideYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 86a by using N-(2,4-dimethoxybenzyl)-1,3,4-thiadiazol-2-amine (WO 2010/079443; 1.00 g, 3.98 mmol), lithium bis(trimethylsilyl)amide (1.0 M solution in THF; 4.78 mL, 4.78 mmol), 2,4-difluoro-5-methylbenzenesulfonyl chloride (WO 2010/079443; 0.989 g, 4.36 mmol) and THF (20 mL), to yield the title compound (1.16 g, 66%) as a colorless amorphous solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-1c3ba42c8e9049ecac52da4cea25ef56
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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