Diisopropylethylamine → HCID 66802145, compound

HRID 528043Notes

Reaction equation

HRID 528043 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.Cl[C:29]1[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[N:31]=[C:32]([C:39]1[CH:40]=[N:41][N:42]([CH2:45][CH3:46])[C:43]=1[CH3:44])[N:33]2[CH3:38]>C(O)C>[CH2:45]([N:42]1[C:43]([CH3:44])=[C:39]([C:32]2[N:33]([CH3:38])[C:34]3[C:30]([N:31]=2)=[C:29]([N:3]2[CH2:4][CH2:5][CH:6]([N:9]4[C:17]5[C:12](=[N:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]4=[O:18])[CH2:7][CH2:8]2)[N:37]=[CH:36][N:35]=3)[CH:40]=[N:41]1)[CH3:46]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 867117136-Chloro-8-(1-ethyl-5-methyl-1H-pyrazol-4-yl)-9-methyl-9H-purine

Product 1

HCID 66802145HCID 66802145, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-piperidin-4-yl-1,3-dihydro-2H-imidazolo[4,5-b]pyridin-2-one dihydrochloride (0.22 g, 0.78 mmol) in an anhydrous ethanol (8 mL) and diisopropylethylamine (0.56 mL) was added 6-chloro-8-(1-ethyl-5-methyl-1H-pyrazol-4-yl)-9-methyl-9H-purine (0.18 g, 0.65 mmol). The reaction mixture was heated to 75° C. for 18 hours. The resulting solution was cooled to room temperature, and concentrated under reduced pressure. The solids were dissolved in dichloromethane (15 mL), and the solution was washed with water (10 mL). The organic layer was concentrated under reduced pressure. The resulting solids were collected by vacuum filtration, and triturated with 5 mL of ethanol at 75° C. for 30 min. The precipitate was collected by vacuum filtration to give 218 mg (73% yield) of the title compound. 1H-NMR (400 MHz, DMSO-d6): δ 11.54 (s, 1H), 8.25 (s, 1H), 7.95 (s, 1H), 7.85 (d, 1H), 7.47 (d, 1H), 6.92 (dd, 1H), 5.60 (broad s, 2H), 4.55 (m, 1H), 4.14 (q, 2H), 3.77 (s, 3H), 3.22 (m, 2H), 2.51 (s, 3H), 2.26 (m, 2H), 1.86 (d, 2H), 1.33 (t, 3H); MS (EI) for C23H26N10O: 459.3 (MH+).

Workup

  1. temperatureThe resulting solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe solids were dissolved in dichloromethane (15 mL)
  4. washthe solution was washed with water (10 mL)
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. filtrationThe resulting solids were collected by vacuum filtration
  7. customtriturated with 5 mL of ethanol at 75° C. for 30 min
  8. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-187197ecbe4342a9b9436a71baff6b2f
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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