2-(4-Piperidyl)-2-propanol → HCID 68313267, compound

HRID 1530590Notes

Reaction equation

CS(O[CH:6]([C:8]1[CH:21]=[C:20]2[C:11]([O:12][CH2:13][CH2:14][N:15]3[C:19]2=[N:18][C:17]([C:22]2[N:23]([CH:28]([CH3:30])[CH3:29])[CH:24]=[C:25]([CH3:27])[N:26]=2)=[CH:16]3)=[CH:10][CH:9]=1)[CH3:7])(=O)=O.[NH:31]1[CH2:36][CH2:35][CH:34]([C:37]([OH:40])([CH3:39])[CH3:38])[CH2:33][CH2:32]1>O1CCOCC1>[CH:28]([N:23]1[CH:24]=[C:25]([CH3:27])[N:26]=[C:22]1[C:17]1[N:18]=[C:19]2[C:20]3[CH:21]=[C:8]([CH:6]([N:31]4[CH2:36][CH2:35][CH:34]([C:37]([OH:40])([CH3:39])[CH3:38])[CH2:33][CH2:32]4)[CH3:7])[CH:9]=[CH:10][C:11]=3[O:12][CH2:13][CH2:14][N:15]2[CH:16]=1)([CH3:29])[CH3:30]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1-{4-[4-methyl-1-(propan-2-yl)-1H-imidazol-2-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethyl methanesulfonate (12 mg, 0.028 mmol) in dioxane (2 mL) was added 2-(piperidin-4-yl)propan-2-ol (40 mg, 0.280 mmol). The resulting mixture was heated at 90° C. overnight. The solvent was removed under reduce pressure and the residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford 202 (2.5 mg, 18% yield) as a white solid. LCMS (ESI): RT=5.23 min, m/z: 478.4 [M+H+]. 1H NMR (500 MHz, DMSO-d6) δ 8.36 (s, 1H), 7.55 (s, 1H), 7.30-7.28 (d, J=9.0 Hz, 1H), 7.05-7.04 (d, J=8.0 Hz, 1H), 7.02 (s, 1H), 5.48 (m, 1H), 4.52 (s, 4H), 3.57 (m, 1H), 3.21-3.18 (m, 1H), 2.99 (m, 1H), 2.23 (s, 3H), 2.10-1.60 (m, 4H), 1.52-1.47 (m, 10H), 1.35-1.22 (m, 3H), 1.13 (s, 6H)

Workup

customThe solvent was removed
customthe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Sources & evidence

ORD record: ord-c410329ea8054a7eaa6d46693d73c757
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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