Triethylsilane → HCID 77105956, compound

HRID 632481Notes

Reaction equation

HRID 632481 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][C:16]([C:19]3[C:20]([NH2:35])=[N:21][CH:22]=[C:23]([C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[N:30]([CH3:34])[CH:29]=[CH:28]5)[CH:24]=3)=[N:17][N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.O>[CH3:34][N:30]1[C:31]2[C:27](=[CH:26][C:25]([C:23]3[CH:24]=[C:19]([C:16]4[O:15][C:14]([CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[N:18][N:17]=4)[C:20]([NH2:35])=[N:21][CH:22]=3)=[CH:33][CH:32]=2)[CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 90273378HCID 90273378, compound

Product 1

HCID 77105956HCID 77105956, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-{5-[2-amino-5-(1-methyl-1H-indol-5-yl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-piperidine-1-carboxylic acid tert-butyl ester (300 mg, 0.63 mmol) in TFA (2.0 mL) at 0° C. was added triethylsilane (146 mg, 1.26 mmol) drop-wise over a period of 5 min, and stirred for 2 h at 0° C. The reaction was diluted with water (20 mL), neutralized with saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain crude product. Crude product was purified by washing with diethyl ether and hexane to afford the title compound as a yellow solid:

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain crude product
  6. customCrude product was purified
  7. washby washing with diethyl ether and hexane

Sources & evidence

ORD record
ord-b9cb2fa74168471b966f89a47fddf226
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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