HCID 67294734, compound → HCID 67294552, compound

HRID 2369001Notes

Reaction equation

HRID 2369001 reaction equation
[CH3:1][Si:2]([CH3:42])([CH3:41])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([C:17]2[CH2:24][CH:23]3[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:19]([CH2:20][O:21][CH2:22]3)[CH:18]=2)[CH:9]=1.[H][H]>CCOC(C)=O.[Pd]>[CH3:40][Si:37]([CH3:38])([CH3:39])[CH2:36][CH2:35][O:34][CH2:33][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:42])[CH3:41])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:18][CH:19]3[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]([CH2:22][O:21][CH2:20]3)[CH2:24]2)[CH:9]=1

Participants

5

Reactant 2

HCID 67294734HCID 67294734, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67294552HCID 67294552, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]non-6-ene-9-carboxylate (1.27 g, 2.06 mmol) in EtOAc (50 mL) was hydrogenated at 50° C. using 10% Pd/C catalyst (200 mg) and 1 atmospheric hydrogen pressure for 16 h. After filtering off the catalyst, the solvent was evaporated off under reduced pressure and crude material was purified by column chromatography (0-40% hexane-ethyl acetate) to give product tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate (1.1 g) as syn- and anti-mixture. HPLC-MS tR=3.15 min (UV254 nm). Mass calculated for formula C30H53N5O5Si2 619.3; observed MH+ (LCMS) 620.2 (m/z).

Workup

  1. customwas hydrogenated at 50° C.
  2. customfor 16 h
  3. filtrationAfter filtering off the catalyst
  4. customthe solvent was evaporated off under reduced pressure and crude material
  5. customwas purified by column chromatography (0-40% hexane-ethyl acetate)

Sources & evidence

ORD record
ord-010af64e07fc499680e17b2836ed437b
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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