Diisopropylethylamine → HCID 178463532, compound

HRID 1192549Notes

Reaction equation

HRID 1192549 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[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)=[C:14]([CH:29]([NH2:31])[CH3:30])[CH:13]=1.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)=[C:14]([CH:29]([NH:31][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:30])[CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58368683HCID 58368683, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178463532HCID 178463532, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-9H-purine (0.077 g, 0.39 mmol), 1-[4-chloro-1- (3-fluorophenyl)-2-naphthyl]ethanamine (0.058 g, 0.19 mmol), and N,N-diisopropylethylamine (0.067 mL, 0.39 mmol) in ethanol (0.6 mL) was heated at 100° C., in a sealed tube overnight. The volatiles were removed under reduced pressure. The 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 C23H18ClFN5(M+H)+: m/z=418.1; Found: 418.1.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe residue was purified on a RP-HPLC (XBridge C18 column
  3. 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-a33c9a0ab8e64e18a4476f9cceb1c378
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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