Sulfuric acid magnesium salt (1:1) → 3-Benzyl-5-chloro-2-(2-dimethylamino-vinyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

HRID 1795975Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH2:9]([N:16]1[C:21](=[O:22])[C:20]2=[C:23]([Cl:26])[CH:24]=[CH:25][N:19]2[N:18]=[C:17]1[CH3:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O-]S([O-])(=O)=O.[Mg+2]>CN(C=O)C>[CH2:9]([N:16]1[C:21](=[O:22])[C:20]2=[C:23]([Cl:26])[CH:24]=[CH:25][N:19]2[N:18]=[C:17]1[CH:27]=[CH:3][N:4]([CH3:6])[CH3:5])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Dimethylformamide dimethylacetal (20 ml, 152 mmol) was added to a solution of 3-benzyl-5-chloro-2-methyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (9.0 g, 33 mmol) in DMF (100 mL) with MgSO4 (5 g) and the reaction mixture was heated to 140° C. in a sealed tube for 16 h. The reaction mixture was concentrated in vacuo, the residue dissolved with EtOAc (50 mL) and a solid was precipitated by addition of petroleum ether (300 mL). The solid was filtered, washed with petroleum ether and dried in vacuo to afford title compound (5.4 g, 50%) as a solid: 1H NMR (CDCl3) δ 7.22 (d, 1H, J=12.43 Hz), 7.08–7.19 (m, 5H), 6.97 (m, 1H), 6.23 (m, 1H), 5.08 (s, 2H), 4.40 (d, 1H, J=12.49 Hz), 2.67 (s, 6H); MS (ESI+) 329 (M++H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutionthe residue dissolved with EtOAc (50 mL)
customa solid was precipitated by addition of petroleum ether (300 mL)
filtrationThe solid was filtered
washwashed with petroleum ether
customdried in vacuo

Sources & evidence

ORD record: ord-9d49cdfa5b4e420e9025b4bf1e8818de
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030118B2

Reaction notes

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