Benzyl (3R)-piperidin-3-ylcarbamate → HCID 71253342, compound

HRID 1774994Notes

Reaction equation

HRID 1774994 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][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][C@@H:31]([NH:35]C(=O)OCC2C=CC=CC=2)[CH2:30]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:29]5[CH2:34][CH2:33][CH2:32][C@H:31]([NH2:35])[CH2:30]5)[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 1514176Benzyl (3R)-piperidin-3-ylcarbamateHCID 712536623-(6-Fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 71253342HCID 71253342, compoundYield 20%

Procedure

Following the procedures of Example 144, 3-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and (R)-benzyl piperidin-3-ylcarbamate were reacted. The reaction mixture was purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 20.0 mg (20%) of 161 over two steps. ESI MS m/z 372.1 (M+1). 1H NMR (400 MHz, DMSO): 9.30 (s, 1H), 9.21 (s, 1H), 9.00 (s, 1H), 8.60 (s, 1H), 8.48 (m, 1H), 7.66 (s, 1H) 7.53 (m, 1H), 7.46 (s, 1H), 6.87 (d, J=8.5 Hz, 1H), 4.37 (m, 1H), 4.29 (d, J=12.6 Hz, 1H), 3.06-2.97 (m, 1H), 2.79 (d, J=7.6 Hz, 2H), 1.94 (m, 1H), 1.80 (m, 1H), 1.61 (d, J=9.5 Hz, 1H), 1.34 (m, 1H)

Workup

  1. customwere reacted
  2. customThe reaction mixture was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-ff8c71ec56b64a8191de5ab400c48520
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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