Diisopropylethylamine → HCID 178463536, compound

HRID 1192559Notes

Reaction equation

HRID 1192559 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][C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([OH:30])[CH2:26][CH2:25]2)=[C:22]2[C:17]([CH:18]=[CH:19][CH:20]=[N:21]2)=[C:16]([Cl:37])[CH:15]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)C>[Cl:37][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[CH2:25][CH2:26][C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([OH:30])[CH2:28][CH2:29]2)=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 583685331-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]-4-phenylpiperidin-4-olHCID 178419477HCID 178419477, compound

Product 1

HCID 178463536HCID 178463536, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.036 g, 0.18 mmol), 1-[7-(1-aminoethyl)-5-chloroquinolin-8-yl]-4-phenylpiperidin-4-ol (0.035 g, 0.092 mmol), and N,N-diisopropylethylamine (0.032 mL, 0.18 mmol) in ethanol (0.32 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 product as the free base. LCMS calculated for C27H27ClN7O (M+H)+: m/z=500.2; Found: 500.1.

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 product as the free base

Sources & evidence

ORD record
ord-75919b1c311d416296041162b2461976
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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