Hydrochloric Acid → HCID 66632710, compound

HRID 659173Notes

Reaction equation

[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[C:8]([C:10]3[N:11]=[C:12]([CH2:22][NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[CH2:31])[CH:25]=4)[NH:13][C:14]=3[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=3)[CH:7]=[CH:6][C:5]=12.[ClH:32].CCOCC>C(Cl)(Cl)Cl>[ClH:32].[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[C:8]([C:10]3[N:11]=[C:12]([CH2:22][NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[CH2:31])[CH:25]=4)[NH:13][C:14]=3[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=3)[CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 50 °C

Procedure

A stirred suspension of N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methyl)-3-vinylaniline (1.00 g, 2.45 mmol) in anhydrous CHCl3 (12 mL) was heated at 50° C. to give a clear solution. The CHCl3 solution was cooled to 0° C. and, to it, was added 1.0 M HCl in Et2O (7.36 mL, 7.36 mmol). After 5 min, the precipitates were filtered under N2 and dried thoroughly over P2O5 in vacuo to give the titled compound (1.07 g, 98%) as a yellow powder. 1H NMR (400 MHz, DMSO-d6) δ 9.49 (dd, 1H, J=1.6, 0.8 Hz), 8.65 (s, 1H), 7.97 (dd, 1H, J=9.2, 0.8 Hz), 7.86 (dd, 1H, overlapped, J=9.2, 1.6 Hz), 7.85 (t, 1H, overlapped, J=7.8 Hz), 7.65 (d, 1H, J=8.0 Hz), 7.38 (d, 1H, J=7.6 Hz), 7.12 (t, 1H, J=7.8 Hz), 6.91 (t, 1H, J=1.6 Hz), 6.79 (d, 1H, J=7.6 Hz), 6.71 (dd, 1H, J=8.0, 1.6 Hz), 6.64 (dd, 1H, J=17.6, 11.2 Hz), 5.80 (dd, 1H, J=17.6, 0.8 Hz), 5.20 (dd, 1H, J=11.2, 0.8 Hz), 4.79 (s, 2H), 2.51 (s, 3H).

Workup

customto give a clear solution
filtrationthe precipitates were filtered under N2
dry with materialdried thoroughly over P2O5 in vacuo

Sources & evidence

ORD record: ord-ea21621032544484bc6506fc0bc00abb
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080568B1

Reaction notes

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