Triethylamine → HCID 10189117, compound

HRID 1371007Notes

Reaction equation

[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:7]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[N:6]1.[Cl:26][C:27]1[CH:43]=[CH:42][C:30]2[N:31]([CH3:41])[C:32](=[O:40])[N:33]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:29]=2[CH:28]=1.C(N(CC)CC)C>CCO>[Cl:26][C:27]1[CH:43]=[CH:42][C:30]2[N:31]([CH3:41])[C:32](=[O:40])[N:33]([CH:34]3[CH2:39][CH2:38][N:37]([CH2:3][CH:2]([OH:1])[CH2:4][N:5]4[CH:9]=[C:8]([C:10]5[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=5)[C:7]([C:16]5[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=5)=[N:6]4)[CH2:36][CH2:35]3)[C:29]=2[CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[1-oxiranylmethyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-pyridine (68 mg, 0.197 mmol) and 5-chloro-1-methyl-3-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (0.055 g, 0.207 mmol) in EtOH (1 mL) was added triethylamine (0.027 mL, 0.197 mmol). The reaction mixture was heated at 80° C. overnight, concentrated, and purified by column chromatography (silica, 2-10% MeOH/CH2Cl2) to afford the title compound (0.026 g, 22%). MS (electrospray): exact mass calculated for C31H30ClF3N6O2, 611.2 [M+H]+, m/z found, 611.2. 1H NMR (400 MHz, CDCl3): 8.59 (br s, 2H), 8.20 (s, 1H), 7.67 (d, J=8.2 Hz, 2H), 7.61 (d, J=5.9 Hz, 2H), 7.55 (d, J=8.2 Hz, 2H), 7.35 (br s, 1H), 7.09 (dd, J=8.2,1.8 Hz, 1H), 6.89 (d, J=8.2 Hz, 1H), 4.55-4.60 (m, 2H), 4.39 (d, J=14.2, 4.1 Hz, 1H), 4.31 (d, J=14.2, 6.1 Hz, 1H), 3.80-3.90 (m, 2H), 3.37 (s, 3H), 3.18-3.33 (m, 2H), 3.02-3.17 (m, 2H), 2.77-2.95 (m, 2H), 1.99 (t, J=12.4 Hz, 2H).

Workup

concentrationconcentrated
custompurified by column chromatography (silica, 2-10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-28a67c9a6e9143dc90c3243e7f752839
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583155B2

Reaction notes

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