Triethylsilane → HCID 178428496, compound

HRID 1059888Notes

Reaction equation

HRID 1059888 reaction equation
O[CH:2]([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1)[C:3]1[S:7][C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[N:5][C:4]=1[CH3:12].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:2][C:3]2[S:7][C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[N:5][C:4]=2[CH3:12])[CH:18]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 178428529HCID 178428529, compound

Product 1

HCID 178428496HCID 178428496, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(5-(hydroxy-(4-methylpyridin-2-yl)methyl)-4-methylthiazol-2-yl)guanidine (65 mg) and triethylsilane (300 mg) in trifluoroacetic acid (3 ml) was stirred for 48 hours and then evaporated under reduced pressure. Water was added, and the pH was adjusted to 12 with 4N aqueous sodium hydroxide. The resultant mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and-evaporated under reduced pressure. The residue was crystallized from dichloromethane to give N-(5-(4-methylpyridin-2-ylmethyl)-4-methylthiazol-2-yl)-guanidine (27 mg).

Workup

  1. customevaporated under reduced pressure
  2. additionWater was added
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. custom-evaporated under reduced pressure
  7. customThe residue was crystallized from dichloromethane

Sources & evidence

ORD record
ord-42f4baf7ba2a4f408f3f01bc5978500f
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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