Diisopropylethylamine → HCID 178463535, compound

HRID 1192553Notes

Reaction equation

HRID 1192553 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.[Cl:11][C:12]1[CH:21]=[C:20]([CH:22]([NH2:24])[CH3:23])[C:19]([N:25]2[CH2:30][CH2:29][C:28]([F:32])([F:31])[CH2:27][CH2:26]2)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:11][C:12]1[CH:21]=[C:20]([CH:22]([NH:24][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:23])[C:19]([N:25]2[CH2:26][CH2:27][C:28]([F:32])([F:31])[CH2:29][CH2:30]2)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 583686671-[5-Chloro-8-(4,4-difluoropiperidin-1-yl)quinolin-7-yl]ethanamineHCID 178419477HCID 178419477, compound

Product 1

HCID 178463535HCID 178463535, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.0244 g, 0.123 mmol), 1-[5-chloro-8-(4,4-difluoropiperidin-1-yl)quinolin-7-yl]ethanamine (0.020 g, 0.061 mmol), and N,N-diisopropylethylamine (0.021 mL, 0.12 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 desired product. LCMS calculated for C21H21ClF2N7 (M+H)+: m/z=444.1; Found: 444.0.

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)

Sources & evidence

ORD record
ord-60e191d3cb0d488d86edc7787a774191
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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