Triethylsilane → HCID 131714463, compound

HRID 638089Notes

Reaction equation

HRID 638089 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[NH:17][C:16](=[O:18])[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:13]3[C:23](=[O:31])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[N:30]=[C:12]23)=[CH:2]1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[OH2:18].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][CH:11]2[NH:17][C:16](=[O:18])[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:13]3[C:23](=[O:31])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[N:30]=[C:12]23)[CH2:2]1.[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][CH:11]2[NH:17][C:16](=[O:18])[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:13]3[C:23](=[O:31])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[N:30]=[C:12]23)[CH2:2]1

Participants

4

Reactant 2

HCID 12052Triethylsilane2×HCID 13603553HCID 13603553, compound

Product 1

HCID 131714463HCID 131714463, compoundYield 123.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-[(1H-Indol-3-yl)methyl]quinazolino(3,2-A)-1,4-benzodiazepin-5,13-(6H,7H)-dione (250 mg, 0.61 mmole) was dissolved in 2 ml of trifluoroacetic acid and treated in one portion with 106 μl (0.67 mmole) of triethylsilane under nitrogen. After 1 hour, 1 mmole more of triethylsilane was added and rapid stirring was continued overnight. Solvent and excess reagent were removed under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with sodium bicarbonate solution and brine, then dried and concentrated. The resulting residue was purified by thick layer silica gel chromatography (9:1 ethyl acetate-hexane v/v) to give a white solid (yield 210 mg) as a mixture of diastereomers (approximately 58:42 HPLC). PMR (360 MHz, CD3OD): spectrum confirms structure assignment.

Workup

  1. waitwas continued overnight
  2. customSolvent and excess reagent were removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. washThe organic phase was washed with sodium bicarbonate solution and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by thick layer silica gel chromatography (9:1 ethyl acetate-hexane v/v)

Sources & evidence

ORD record
ord-40aacca7710146c0b8a929da377a32dd
Source dataset
uspto-grants-1985_12
Patent number
US04559339

Reaction notes

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