Diisopropylethylamine → HCID 178463534, compound

HRID 1192556Notes

Reaction equation

HRID 1192556 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[NH2:11][CH:12]([C:14]1[C:23]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([OH:30])[CH2:25]2)=[C:22]2[C:17]([CH:18]=[CH:19][CH:20]=[N:21]2)=[C:16]([Cl:31])[CH:15]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)C>[Cl:31][C:16]1[CH:15]=[C:14]([CH:12]([NH:11][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:13])[C:23]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([OH:30])[CH2:25]2)=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58368684(3S)-1-[7-(1-aminoethyl)-5-chloroquinolin-8-yl]piperidin-3-olHCID 178419477HCID 178419477, compound

Product 1

HCID 178463534HCID 178463534, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.0234 g, 0.118 mmol), (3S)-1-[7-(1-aminoethyl)-5-chloroquinolin-8-yl]piperidin-3-ol (0.018 g, 0.059 mmol), and N,N-diisopropylethylamine (0.0205 mL, 0.118 mmol) in ethanol (0.2 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resulting residue was purified on a RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min) to give the products. First peak retention time 1.482 minutes, LCMS calculated for C21H23ClN7O (M+H)+: m/z=424.2; Found: 424.0. Second peak retention time 1.583 minutes, LCMS calculated for C21H23ClN7O (M+H)+: m/z=424.2; Found: 424.0.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. customthe resulting residue was purified on a RP-HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min)
  6. customto give the products

Sources & evidence

ORD record
ord-016bb599b4e241d2b4379727dd8e0a26
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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