(3R)-3-Aminopiperidine, 3-BOC protected → HCID 71253763, compound

HRID 1775085Notes

Reaction equation

HRID 1775085 reaction equation
F[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][N:20]([CH2:22][CH3:23])[CH:21]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH:36]C(=O)OC(C)(C)C)[CH2:31]1>>[CH2:22]([N:20]1[CH:21]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([C:6]4[N:7]=[C:2]([N:30]5[CH2:35][CH2:34][CH2:33][C@@H:32]([NH2:36])[CH2:31]5)[CH:3]=[CH:4][CH:5]=4)=[N:9][NH:10][C:11]3=[CH:12][N:13]=2)[CH:18]=[N:19]1)[CH3:23]

Participants

3

Reactant 2

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 71254031HCID 71254031, compound

Product 1

HCID 71253763HCID 71253763, compoundYield 41.6%

Procedure

Following the procedures as described in Example 189, 3-(6-fluoropyridin-2-yl)-5-(1-ethyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and (R)-tert-butyl piperidin-3-ylcarbamate were reacted. The product was deprotected and purified to give 285 as a white solid (41.6% over two steps). 1H NMR (400 MHz, DMSO) δ 9.02 (s, 1H), 8.60 (s, 1H), 8.34 (s, 1H), 7.97 (s, 1H), 7.62 (t, J=8.0 Hz, 1H), 7.42 (d, J=7.4 Hz, 1H), 6.83 (d, J=8.5 Hz, 1H), 4.45 (d, J=8.7 Hz, 1H), 4.28-4.12 (m, 3H), 2.98 (t, J=10.9 Hz, 1H), 2.82-2.72 (m, 2H), 2.03-1.93 (m, 1H), 1.86-1.77 (m, 1H), 1.67-1.51 (m, 1H), 1.42 (t, J=7.3 Hz, 3H), 1.38-1.26 (m, 1H); 3 protons not seen. LC/MS: m/z 389.2 [M+1]

Workup

  1. customwere reacted
  2. custompurified

Sources & evidence

ORD record
ord-b47afed6a23d4c5e82f2a000fc688de5
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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