Acetyl chloride → HCID 57567334, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].CCN(C(C)C)C(C)C.[C:32](Cl)(=[O:34])[CH3:33].N1CCCCC1>C1COCC1.C(Cl)Cl>[C:32]([NH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8])(=[O:34])[CH3:33]Participants
Procedure
To a solution of N-(3-amino-4-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (167) (33 mg, 0.11 mmol) and DIEA (49 μL, 0.28 mmol) in THF (1 mL) was added acetyl chloride (16 μL, (0.22 mmol). The reaction was stirred at room temperature for 30 min. LCMS analysis indicated that diacylation had occurred. A solution of piperidine (81 μL, 0.82 mmol) in CH2Cl2 (2 mL) was added and the reaction stirred for a further 30 min at which time only the desired product was detected by LCMS. The reaction solution was concentrated and the residue was dissolved in DMSO and purified by HPLC (10-99% CH3CN/H2O) to yield the product, N-(3-acetylamino-4-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (248) (4 mg, 11%). 1H NMR (400 MHz, DMSO-d6) δ 12.95 (d, J=6.6 Hz, 1H), 12.42 (s, 1H), 9.30 (s, 1H), 8.86 (d, J=6.8 Hz, 1H), 8.33 (dd, J=8.1, 1.3 Hz, 1H), 7.85-7.81 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.55 (t, J=8.1 Hz, 1H), 7.49 (dd, J=8.2, 2.2 Hz, 1H), 7.18 (d, J=8.3 Hz, 1H), 2.18 (s, 3H), 2.08 (s, 3H); HPLC ret. time 2.46 min, 10-99% CH3CN, 5 min run; ESI-MS 336.3 m/z (MH+).
Sources & evidence
- ORD record
- ord-e805cd26eff140248aa6348535083f63
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495103B2
Reaction notes
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