Triethylsilane → HCID 42601461, compound

HRID 334997Notes

Reaction equation

HRID 334997 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)O)[CH:14]=[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=3)[C:11]=2[N:12]=1)(C)(C)C.[SiH](CC)(CC)CC>>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:17][C:15]2[CH:14]=[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=3)[C:11]3[N:12]=[C:8]([NH2:7])[S:9][C:10]=3[CH:16]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 12052TriethylsilaneHCID 57695175HCID 57695175, compound

Product 1

HCID 42601461HCID 42601461, compoundYield 83.9%

Procedure

BA-01. A solution of compound (7) (32.5 mg, 0.066 mmol) was treated with Et3SiH (500 uL, 3 mmol, 47 eq.). The mixture was stirred at room temperature for 130 min. until starting material XM-17 was consumed. The volatile material was removed under reduced pressure. The residue was washed with sodium bicarbonate solution, extracted with EtOAc (3×15 mL), dried. Evaporation gave a residue, which was purified chromatography on silica gel using dichloromethane/hexanes (1:1, 2:1, 3:1, 4:1, 20 mL each) followed by dichloromethane as eluent to give 21 mg of product, which contained impurities. The product thus obtained was triturated with hexanes to give 7.6 mg of desired product. BA-01. 1H NMR. LCMS: 99%.

Workup

  1. customwas consumed
  2. customThe volatile material was removed under reduced pressure
  3. washThe residue was washed with sodium bicarbonate solution
  4. extractionextracted with EtOAc (3×15 mL)
  5. customdried
  6. customEvaporation
  7. customgave a residue, which
  8. customwas purified chromatography on silica gel

Sources & evidence

ORD record
ord-58a52b3d71fc4110a99177201a36be38
Source dataset
uspto-grants-2014_11
Patent number
US08883833B2

Reaction notes

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