Diisopropylethylamine → HCID 68157574, compound

HRID 243149Notes

Reaction equation

HRID 243149 reaction equation
Cl.Cl.[Br:3][C:4]1[C:9]2[N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]([C@@H:13]([NH2:15])[CH3:14])=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl[C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][N:27]2[CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1.CCN(C(C)C)C(C)C>CC(O)C>[Br:3][C:4]1[C:9]2[N:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11]([C@@H:13]([NH:15][C:23]3[N:31]=[CH:30][N:29]=[C:28]4[C:24]=3[N:25]=[CH:26][N:27]4[CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[CH3:14])=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 68157452(S)-1-(7-Bromo-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

Product 1

HCID 68157574HCID 68157574, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(S)-1-(7-Bromo-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride (1 g, 2.5 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.736 g, 3.1 mmol) and DIPEA (2.26 mL, 13 mmol) in IPA (4 mL) were heated in a sealed tube for 4 h. The cooled reaction mixture was concentrated in vacuo; the residue dissolved in EtOAc and the resulting solution washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified on silica (Si—PCC, 0-10% MeOH in DCM) to give the product as a white solid (870 mg, 67%). LCMS (Method B): RT 3.48 min; m/z [M+H]+ 518/520

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. washthe resulting solution washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica (Si—PCC, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-2758b3bfad1e4413be41f2573fa5e27c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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