Isopropanol → 1-{1-[8-(1-Ethyl-1H-pyrazol-4-yl)-9-methyl-9H-purin-6-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one

HRID 528037Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.C(O)(C)C.Cl[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[N:24]=[C:25]([C:32]1[CH:33]=[N:34][N:35]([CH2:37][CH3:38])[CH:36]=1)[N:26]2[CH3:31]>C(N(CC)CC)C>[CH2:37]([N:35]1[CH:36]=[C:32]([C:25]2[N:26]([CH3:31])[C:27]3[C:23]([N:24]=2)=[C:22]([N:1]2[CH2:2][CH2:3][CH:4]([N:7]4[C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[NH:9][C:8]4=[O:16])[CH2:5][CH2:6]2)[N:30]=[CH:29][N:28]=3)[CH:33]=[N:34]1)[CH3:38]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-piperidin-4-yl-1,3-dihydro-2H-benzimidazol-2-one (0.1 g, 0.33 mmol) in an anhydrous isopropanol (8 mL) and triethylamine (0.2 mL) was added 6-chloro-8-(1-ethyl-1H-pyrazol-4-yl)-9-methyl-9H-purine (65 mg, 0.25 mmol). The reaction mixture was heated to 80° C. for 16 hours, and cooled to room temperature. The resulting precipitates were collected by vacuum filtration, and triturated with 15 mL of ethanol at 75° C. for 30 min. The solids were collected by vacuum filtration to give 107 mg (97% yield) of the title compound. 1H-NMR (400 MHz, DMSO-d6): δ 10.86 (s, 1H), 8.44 (s, 1H), 8.25 (s, 1H), 8.03 (d, 1H), 7.13 (dd, 1H), 6.93 (m, 3H), 5.61 (s, 2H), 4.53 (dd, 1H), 4.22 (q, 2H), 3.84 (s, 3H), 3.18 (s, 2H), 2.33 (m, 2H), 1.82 (d, 2H), 1.40 (t, 3H); MS (EI) for C23H25N9O: 444.3 (MH+).

Workup

temperaturecooled to room temperature
customThe resulting precipitates
filtrationwere collected by vacuum filtration
customtriturated with 15 mL of ethanol at 75° C. for 30 min
filtrationThe solids were collected by vacuum filtration

Sources & evidence

ORD record: ord-c7949617548c4f1ebffaf5c8fa7b9d2e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346807B2

Reaction notes

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