Sulfuric Acid → HCID 66633048, compound

HRID 659174Notes

Reaction equation

HRID 659174 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.[OH:32][S:33]([OH:36])(=[O:35])=[O:34]>CCO.CCOCC>[S:33]([OH:36])([OH:35])(=[O:34])=[O: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

5

Reactant 2

HCID 1118Sulfuric AcidHCID 54766775HCID 54766775, compound

Product 1

HCID 66633048HCID 66633048, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To 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 (100 mg, 0.25 mmol) in anhydrous EtOH (2 mL) at 0° C. was added 10% H2SO4 in anhydrous EtOH (0.20 mL, 0.37 mmol). The mixture was allowed to warm to room temperature and stirred for 10 min. The reaction mixture was diluted with anhydrous Et2O (8 mL) and stirred for an additional 10 min. The precipitates were filtered under N2, washed with anhydrous Et2O (4×4 mL), and then dried thoroughly over P2O5 in vacuo to give the titled compound (79 mg, 64%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.40 (dd, 1H, J=1.6, 0.8 Hz), 8.63 (s, 1H), 7.98 (dd, 1H, J=9.2, 0.8 Hz), 7.84 (t, 1H, J=8.0 Hz), 7.76 (dd, 1H, J=9.2, 1.6 Hz), 7.43 (d, 1H, J=7.6 Hz), 7.40 (d, 1H, J=8.0 Hz), 7.13 (t, 1H, J=7.8 Hz), 6.80 (br s, 1H), 6.79 (d, 1H, overlapped, J=7.6 Hz), 6.64 (dd, 1H, overlapped, J=17.6, 11.2 Hz), 6.63 (dd, 1H, overlapped, J=7.6, 2.0 Hz), 5.74 (dd, 1H, J=17.6, 0.8 Hz), 5.21 (dd, 1H, J=11.2, 0.8 Hz), 4.68 (s, 2H), 2.58 (s, 3H).

Workup

  1. stirringstirred for an additional 10 min
  2. filtrationThe precipitates were filtered under N2
  3. washwashed with anhydrous Et2O (4×4 mL)
  4. dry with materialdried thoroughly over P2O5 in vacuo

Sources & evidence

ORD record
ord-3a61b91243ed4ce3af3d3391cb56d76e
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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