Diisopropylethylamine → HCID 178432788, compound

HRID 1192542Notes

Reaction equation

HRID 1192542 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.[F:11][C:12]1[CH:13]=[C:14]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH3:28])=[N:20][C:19]=2[CH:29]([NH2:31])[CH3:30])[CH:15]=[CH:16][CH:17]=1.C(N(CC)C(C)C)(C)C>C(O)C>[F:11][C:12]1[CH:13]=[C:14]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH3:28])=[N:20][C:19]=2[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:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58368483HCID 58368483, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178432788HCID 178432788, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-9H-purine (0.31 g, 1.6 mmol), 1-[4-(3-fluorophenyl)-1-methylisoquinolin-3-yl]ethanamine (0.220 g, 0.785 mmol), and N,N-diisopropylethylamine (0.27 mL, 1.57 mmol) in ethanol (3 mL) was heated at 100° C. in a sealed tube overnight. The mixture was filtered and filtrate evaporated to dryness under reduced pressure. 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 as the free base. LCMS calculated for C23H20FN6 (M+H)+: m/z=399.2; Found: 399.1.

Workup

  1. filtrationThe mixture was filtered
  2. customfiltrate evaporated to dryness under reduced pressure
  3. customThe resulting residue was purified on a RP-HPLC (XBridge C18 column
  4. 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-997eebf51bd243e986e63f973cc203ed
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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