Tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate → 5-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one

HRID 2369004Notes

Reaction equation

HRID 2369004 reaction equation
C[Si](C)(C)CCOC[N:7]([CH2:50]OCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:36][CH:35]3[N:37](C(OC(C)(C)C)=O)[CH:31]([CH2:32][O:33][CH2:34]3)[CH2:30]2)[C:9]=1[C:45]([O:47]CC)=[CH2:46]>C(O)(C(F)(F)F)=O>[CH:31]12[NH:37][CH:35]([CH2:36][CH:29]([C:10]3[C:9]4[C:45](=[O:47])[CH2:46][CH2:50][NH:7][C:8]=4[N:13]4[N:14]=[CH:15][C:16]([C:17]5[CH:18]=[N:19][C:20]([C:23]6[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=6)=[CH:21][CH:22]=5)=[C:12]4[N:11]=3)[CH2:30]1)[CH2:34][O:33][CH2:32]2

Participants

3

Reactant 1

HCID 86686739Tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate

Product 1

HCID 1364047575-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate was treated with anhydrous TFA (10 mL) at rt and the mixture was stirred for 16 h. Then the solvent was evaporated off under reduced pressure and the material was lyophilized from acetonitrile:water (3:1) to give compound 5-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one as yellow solid (122 mg) which was used without further purification. HPLC-MS tR=1.16 min (UV254 nm). Mass calculated for formula C26H26N6O2 454.2; observed MH+ (LCMS) 455.2 (m/z).

Workup

  1. customThen the solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-978f11d1f97d4c2fbdcdf9aae72822ae
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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