Ammonium Acetate → 2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine
Reaction equation
O=[C:2]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]1[C:10](=O)[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[NH:7][C:6]2[N:16]=[CH:17][CH:18]=[CH:19][C:5]1=2.C([O-])(=O)C.[NH4+:32]>C(O)(=O)C>[CH2:20]([C:2]1[N:32]=[C:10]2[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[NH:7][C:6]3[N:16]=[CH:17][CH:18]=[CH:19][C:5]=3[N:4]2[CH:3]=1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 5-(2-oxo-4-phenylbutyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one (1.56 g, 1 eq.) in acetic acid (10 mL) was added ammonium acetate (3.37 g, 10 eq.). The reaction was stirred at 120° C. for 8 hours. The reaction mixture was poured onto water (100 mL) and extracted with dichloromethane (3×100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (0-10% methanol in dichloromethane) gave the 2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.374 g, 27%). 1H NMR (CDCL3) 400 MHz δ 8.08 (dd, JA=4.8 Hz, JB=1.6 Hz, 1H), 7.97 (dd, JA=8.0 Hz, JB=1.2 Hz, 1H), 7.46 (dd, JA=8.0 Hz, JB=1.6 Hz, 1H), 7.34-7.15 (m, 6H), 7.08 (td, JA=7.6 Hz, JB=1.2 Hz, 1H), 6.98 (dd, JA=7.6 Hz, JB=4.8 Hz, 1H), 6.86 (dd, JA=7.6 Hz, JB=0.8 Hz, 1H), 6.81 (s, 1H), 6.27 (s, 1H), 3.07-2.90 (m, 4H); LCMS: 339 [M+H].
Workup
- additionThe reaction mixture was poured onto water (100 mL)
- extractionextracted with dichloromethane (3×100 mL)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customPurification by column chromatography (0-10% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-02d438b9d8514cf7976d6e26566105b4
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569331B2
Reaction notes
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