Tert-Butylamine → N-tert-butyl-2-(5-fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxamide
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]([OH:27])=O)[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:28]=1.C(N(CC)CC)C.[CH3:36][C:37]([NH2:40])([CH3:39])[CH3:38].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl>[C:37]([NH:40][C:25]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:8]1[O:9][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:28][C:6]=3[CH:7]=1)[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18]2)=[O:27])([CH3:39])([CH3:38])[CH3:36]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(5-fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid (486 mg, 1.28 mmol) in dichloromethane (30 ml) was added triethylamine (366 mg, 3.62 mmol), 2-methylpropan-2-amine (212 mg, 2.90 mmol) and T3P (610 mg, 1.92 mmol), and the resulting mixture was stirred for 1 h at room temperature. The reaction mixture was then quenched with water (120 ml), extracted with dichloromethane (4×60 ml), and the organic layers combined and concentrated in vacuo to afford N-tert-butyl-2-(5-fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxamide as a yellow solid (600 mg, crude), which was used to the next step without further purification.
Workup
- customThe reaction mixture was then quenched with water (120 ml)
- extractionextracted with dichloromethane (4×60 ml)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a82bad7676c84aaea05dbd5b5f696397
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916561B2
Reaction notes
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