Methanol → N-isopropyl-2-(3-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)azetidin-1-yl)acetamide
Reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[CH:27]=[CH:26][C:9]3[C:10]4[N:14]([CH2:15][CH2:16][O:17][C:8]=3[CH:7]=2)[CH:13]=[C:12]([C:18]2[N:19]([CH:23]([CH3:25])[CH3:24])[N:20]=[CH:21][N:22]=2)[N:11]=4)[CH2:3]1.Cl[CH2:29][C:30]([NH:32][CH:33]([CH3:35])[CH3:34])=[O:31].CO>O>[CH:33]([NH:32][C:30](=[O:31])[CH2:29][N:2]1[CH2:3][CH:4]([C:6]2[CH:27]=[CH:26][C:9]3[C:10]4[N:14]([CH:13]=[C:12]([C:18]5[N:19]([CH:23]([CH3:24])[CH3:25])[N:20]=[CH:21][N:22]=5)[N:11]=4)[CH2:15][CH2:16][O:17][C:8]=3[CH:7]=2)[CH2:5]1)([CH3:35])[CH3:34]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Following the procedure for 143, 8-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene hydrochloride (Example 65) was reacted with 2-chloro-N-isopropyl acetamide. The crude product was subjected to reverse phase HPLC (Gemini C18 column gradient 0 to 70% MeOH in H2O+0.1% HCO2H) to give 200 as a white solid. 1H NMR δ (ppm)(CDCl3): 8.46 (1 H, d, J=8.28 Hz), 7.85 (1 H, s), 7.63 (1 H, s), 7.05 (1 H, dd, J=8.32, 1.82 Hz), 6.94-6.92 (1 H, m), 6.00-5.90 (1 H, m), 4.49-4.40 (4 H, m), 4.12-4.02 (1 H, m), 3.88 (2 H, t, J=7.51 Hz), 3.82-3.71 (1 H, m), 3.41 (2 H, t, J=7.23 Hz), 3.23 (2 H, s), 1.56 (6 H, d, J=6.63 Hz), 1.16 (6 H, d, J=6.57 Hz). 1 Exchangeable proton not seen. LCMS: RT=6.8 min, M+H+=450
Sources & evidence
- ORD record
- ord-86d4e98d600d41f1ba3baf7072f3c66d
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785626B2
Reaction notes
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