Tert-butyl 3-oxopiperazine-1-carboxylate → 1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-one

HRID 1775108Notes

Reaction equation

HRID 1775108 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10](COCC[Si](C)(C)C)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[O:31]=[C:32]1[NH:37][CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33]1>>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([C:6]4[N:7]=[C:2]([N:37]5[CH2:36][CH2:35][NH:34][CH2:33][C:32]5=[O:31])[CH:3]=[CH:4][CH:5]=4)=[N:9][NH:10][C:11]3=[CH:12][N:13]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 866767023-(6-Bromopyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712533401-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-oneYield 20%

Procedure

Following the procedure of Example 224, 3-(6-bromopyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and tert-butyl 3-oxopiperazine-1-carboxylate were reacted. The product was deprotected by the procedure of Example 225 and purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 8.0 mg (20%) of 301 over two steps. ESI MS m/z 372.1 (M+1). 1H NMR (400 MHz, DMSO); 14.08 (s, 1H), 9.29 (d, J=2.0 Hz, 1H), 9.25 (s, 1H), 8.94 (s, 1H), 8.61 (dd, J=4.7, 1.3 Hz, 1H), 8.47-8.40 (m, 1H), 8.07-7.92 (m, 3H), 7.56 (dd, J=7.9, 4.8 Hz, 1H), 6.48 (s, 1H), 4.22 (t, J=5.4 Hz, 2H), 3.56 (s, 2H), 3.18 (t, J=5.4 Hz, 2H). m/z 372.1 (M+1)

Workup

  1. customwere reacted
  2. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-c37b976e162e48f5a6eace17091cc41f
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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