HCID 57707840, compound → HCID 57708002, compound

HRID 1397685Notes

Reaction equation

HRID 1397685 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])=[N+]=[N-]>CO.[Pd]>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[N:7]=[C:6]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:5]([CH2:4][NH2:1])=[CH:14]2

Participants

4

Reactant 1

HCID 57707840HCID 57707840, compound

Product 1

HCID 57708002HCID 57708002, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(Azidomethyl)-8-chloro-2-(piperidin-1-yl)quinoline (30 mg, 0.1 mmol) was dissolved in MeOH (1 mL) and treated with 10% Pd—C (5 wt %) and the mixture was then stirred under H2 balloon over night. The mixture was filtered through a Celite™ pad followed by removal of solvents to give (8-chloro-2-(piperidin-1-yl)-quinolin-3-yl)methanamine as a colorless oil. N-((8-chloro-2-(piperidin-1-yl)-quinolin-3-yl)methyl)-9H-purin-6-amine was prepared according to Procedure H. 1H NMR (400 MHz, CDCl3) δ ppm 8.29 (s, 1H), 7.79 (m, 3H), 7.45 (m, 2H), 5.43 (2H, s), 3.90 (m, 4H), 2.23 (m, 4H), 1.84 (m, 2H). Mass Spectrum (ESI) m/e=394 (M+1).

Workup

  1. filtrationThe mixture was filtered through a Celite™ pad
  2. customfollowed by removal of solvents

Sources & evidence

ORD record
ord-30d2e4147f07432ea1f7fa55549ab103
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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