Diisopropylethylamine → HCID 178505517, compound

HRID 1397727Notes

Reaction equation

HRID 1397727 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(N(C(C)C)CC)(C)C.[F:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:27]([CH2:37][NH2:38])=[CH:26]2>C(O)CCC>[F:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:27]([CH2:37][NH:38][C:2]1[N:10]=[CH:9][N:8]=[C:7]3[C:3]=1[N:4]=[CH:5][NH:6]3)=[CH:26]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5287830Purine, 6-bromo-HCID 57707794(8-Fluoro-2-phenylquinolin-3-yl)methanamine

Product 1

HCID 178505517HCID 178505517, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

To a reaction flask was added 6-bromopurine (19 mg, 95 μmol, 1.2 eq), diisopropylethylamine (42 μl, 238 μmol, 3 eq), (8-fluoro-2-phenylquinolin-3-yl)-methanamine (20 mg, 79 μmol, 1 eq), and n-butanol (0.75 mL). The reaction was heated to 110° C. for 8 h. The reaction was cooled to rt and the solvent was removed in vacuo. The compound was purified by reverse phase HPLC. The fractions were concentrated and freebased with sat. NaHCO3. The organic layer was extracted into DCM, dried over MgSO4, filtered, and concentrated to afford a white solid,

Workup

  1. temperatureThe reaction was cooled to rt
  2. customthe solvent was removed in vacuo
  3. customThe compound was purified by reverse phase HPLC
  4. concentrationThe fractions were concentrated
  5. extractionThe organic layer was extracted into DCM
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a white solid

Sources & evidence

ORD record
ord-5fb8ecf7370549aa9d724a79eb91e7d6
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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