4-(3-amino-1,2,4-triazin-6-yl)-N,2-dimethylbenzamide → N,2-dimethyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide

HRID 1508285Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH3:18])[CH:9]=2)=[CH:6][N:7]=1.Cl[CH:20]([CH2:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][CH:28]=[CH:27]2)[CH:21]=O>C(O)C>[CH3:15][NH:14][C:12](=[O:13])[C:11]1[CH:16]=[CH:17][C:8]([C:5]2[CH:6]=[N:7][C:2]3[N:3]([C:20]([CH2:23][C:24]4[CH:25]=[C:26]5[C:31](=[CH:32][CH:33]=4)[N:30]=[CH:29][CH:28]=[CH:27]5)=[CH:21][N:1]=3)[N:4]=2)=[CH:9][C:10]=1[CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(3-amino-1,2,4-triazin-6-yl)-N,2-dimethylbenzamide (Step 3, 0.30 g, 1.2 mmol) and 2-chloro-3-quinolin-6-ylpropanal (Step 4, 0.32 g, 1.5 mmol) in ethanol (2.5 mL) in a sealed tube was stirred at 120° C. overnight. After cooling, the reaction mixture was purified by RP-HPLC (pH=2) to afford the desired product (150 mg) as the TFA salt. LCMS (M+H)+: m/z=409.3. 1H-NMR (400 MHz, CD3OD): 9.64 (s, 1H), 9.21 (d, J=5.0, 1H), 9.18 (d, J=8.0 Hz, 1H), 8.44 (s, 1H), 8.39 (s, 1H), 8.32 (d, J=9.0 Hz, 11H), 8.27 (d, J=8.0 Hz, 1H), 8.12 (dd, J=9.0, 5.0, Hz, 1H), 8.05 (s, 1H), 8.03 (s, 1H), 7.57 (d, J=8.0 Hz, 1H), 4.86 (s, 2H), 2.92 (s, 3H), 2.48 (s, 3H).

Workup

temperatureAfter cooling
customthe reaction mixture was purified by RP-HPLC (pH=2)

Sources & evidence

ORD record: ord-f518045a27b9445183ace4ec3384c137
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221824B2

Reaction notes

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