Diisopropylethylamine → HCID 178463530, compound

HRID 1192462Notes

Reaction equation

HRID 1192462 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)[CH:21]=[CH:20][C:19]=2[CH:28]([NH2:30])[CH3:29])[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)[CH:21]=[CH:20][C:19]=2[CH:28]([NH:30][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:29])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67301543HCID 67301543, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178463530HCID 178463530, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.02696 g, 0.1355 mmol), 1-[1-(3-fluorophenyl)-2-naphthyl]ethanamine (0.030 g, 0.11 mmol), and N,N-diisopropylethylamine (0.024 mL, 0.14 mmol) in ethanol (0.9 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resultant residue was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/minute) to give the product as a TFA salt. LCMS calculated for C23H19FN5(M+H)+: m/z=384.2; found: 384.3. 1H NMR (DMSO-d6, 400 MHz) δ 8.92 (1H, br s), 8.30 (2H, m), 7.97 (1H, d, J=9.2 Hz), 7.90 (1H, d, J=7.6 Hz), 7.79 (1H, m), 7.57 (1H, m), 7.47 (1H, m), 7.40 (2H, m), 7.31 (1H, m), 7.19 (2H, m), 5.23 (1H, m), 1.49 (3H, m) ppm. 19F NMR (DMSO-d6, 376.28 MHz) δ −74.6 ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. customthe resultant residue was purified on RP-HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/minute)

Sources & evidence

ORD record
ord-ee03bfc1467b419c842627df34c02439
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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