Diisopropylethylamine → HCID 178463551, compound

HRID 1192576Notes

Reaction equation

HRID 1192576 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[CH:15]=[C:16]([C:31]#[N:32])[C:17]2[CH:18]=[CH:19][CH:20]=[N:21][C:22]=2[C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)C>[F:30][C:26]1[CH:25]=[C:24]([C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]([C:31]#[N:32])=[CH:15][C:14]=2[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])[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58368544HCID 58368544, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178463551HCID 178463551, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.0246 g, 0.124 mmol), 7-(1-aminoethyl)-8-(3-fluorophenyl)quinoline-5-carbonitrile (0.018 g, 0.062 mmol), and N,N-diisopropylethylamine (0.0216 mL, 0.124 mmol) in ethanol (0.2 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resulting mixture 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 C23H17FN7 (M+H)+: m/z =410.2; Found: 410.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. customthe resulting mixture 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-8c3fcb33eb114e1ead358168e76660ac
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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