2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → HCID 72949481, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[NH2:5].C[Al](C)C.[NH:18](/[C:22](/[CH3:28])=[CH:23]\[C:24](OC)=[O:25])[C:19]([CH3:21])=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:24](=[O:25])[CH:23]=[C:22]([CH3:28])[N:18]=[C:19]2[CH3:21])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1Participants
Procedure
To a solution of 3-fluoro-4-(pyrrolidin-1-yl)aniline (0.50 g, 2.78 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (14 mL, 14 mmol, 1 M in heptane) slowly at rt. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (480 mg, 3.06 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred at rt for 3 days, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (100 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (300 mg, 38%). The compound was characterized by the following spectroscopic data:
Workup
- stirringThe reaction mixture was stirred at rt for 3 days
- customquenched with saturated NH4Cl aqueous solution
- extractionextracted with CH2Cl2 (100 mL×3)
- dry with materialThe combined organic phases were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)
Sources & evidence
- ORD record
- ord-bb9c95e0c82a44628a12af0371a83d39
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
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