(3R)-3-Aminopiperidine, 3-BOC protected → (R)-1-(4-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyrimidin-2-yl)piperidin-3-amine

HRID 1775106Notes

Reaction equation

HRID 1775106 reaction equation
Cl[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][N:3]=1.[NH:31]1[CH2:36][CH2:35][CH2:34][C@@H:33]([NH:37]C(=O)OC(C)(C)C)[CH2:32]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[CH:5]=[CH:4][N:3]=[C:2]([N:31]5[CH2:36][CH2:35][CH2:34][C@@H:33]([NH2:37])[CH2:32]5)[N:7]=4)=[N:9][NH:10][C:11]3=[CH:12][N:13]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 866767013-(2-Chloropyrimidin-4-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 71254093(R)-1-(4-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyrimidin-2-yl)piperidin-3-amineYield 63%

Procedure

Following the procedure of Example 144, 3-(2-chloropyrimidin-4-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and (R)-tert-butyl piperidin-3-ylcarbamate 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 32 mg (63%) of 300. ESI MS m/z 373.2 (M+1). 1H NMR (400 MHz, DMSO): 9.30 (s, 1H), 9.25 (s, 1H), 8.91 (s, 1H), 8.59 (dd, J=4.7, 1.2 Hz, 1H), 8.45 (t, J=8.1 Hz, 2H), 7.53 (dd, J=7.9, 4.7 Hz, 1H), 7.32 (d, J=5.0 Hz, 1H), 4.71 (d, J=10.8 Hz, 1H), 4.61 (d, J=12.5 Hz, 1H), 3.15-3.06 (m, 1H), 2.91-2.83 (m, 1H), 2.82-2.73 (m, 1H), 1.96 (d, J=11. Hz, 1H), 1.81 (d, J=13.4 Hz, 1H), 1.55 (d, J=12.1 Hz, 1H), 1.36 (td, J=12.2, 3.8 Hz, 1H)

Workup

  1. customwere reacted
  2. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-f4e51a811a134f8f9787adf9dd964960
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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