Diisopropylethylamine → HCID 178461958, compound

HRID 243413Notes

Reaction equation

HRID 243413 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[C@@H:16]([NH2:18])[CH3:17].Cl[C:20]1[N:28]=[CH:27][N:26]=[C:25]2[C:21]=1[N:22]=[CH:23][N:24]2C1CCCCO1.CCN(C(C)C)C(C)C.Cl.O1CCOCC1>CC(O)C>[N:28]1[C:20]([NH:18][C@H:16]([C:8]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH3:17])=[C:21]2[C:25]([NH:24][CH:23]=[N:22]2)=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 204431481,4-Dioxane hydrochlorideHCID 68157317(S)-1-(3-Pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine

Product 1

HCID 178461958HCID 178461958, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (S)-1-(3-pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine (0.134 g, 0.56 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.186 g, 0.78 mmol) and DIPEA (0.18 mL, 1.01 mmol) in IPA (2 mL) was stirred at 90° C. in a sealed tube for 16 h. The resulting mixture was concentrated in vacuo and residue was purified by chromatography (SiO2, 0-10% (2M ammonia in methanol) in DCM). The product was dissolved in methanol and treated with HCl/dioxane (4M, 1.0 mL, 4.00 mol) and stirred for 30 min. The resulting mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH and the product eluted with 2M NH3/MeOH then concentrated in vacuo to give 293 as a white solid (0.160 g, 80%). LCMS (method K): Rt 2.28 min, [M+H]+ 358. 1H NMR (DMSO-d6): δ 13.20-12.70 (1H, bs), 8.59 (1H, s), 8.31 (1H, m), 8.13 (2H, m), 8.03 (2H, tm), 7.81-7.81 (1H, m), 7.47 (1H, s), 7.36 (1H, m), 5.99 (1H, m), 1.67 (3H, d, J=6.82 Hz)

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo and residue
  2. customwas purified by chromatography (SiO2, 0-10% (2M ammonia in methanol) in DCM)
  3. dissolutionThe product was dissolved in methanol
  4. stirringstirred for 30 min
  5. washwashed with MeOH
  6. washthe product eluted with 2M NH3/MeOH
  7. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-f08c9f08490b4fac8dec2b3a8066c9a4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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