Toluene → 4-[2-(tert-Butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[C:16]([F:21])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH2:13][C:12]1=[O:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:32](Cl)(Cl)=[O:33].C1(C)C=CC=CC=1.[NH2:43][CH2:44][C:45]1[CH:65]=[CH:64][C:48]([C:49]([N:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]2OC=CC=2)C)=[O:50])=[CH:47][C:46]=1[CH3:66].[CH2:67]1[CH2:71][O:70][CH2:69][CH2:68]1>>[O:70]1[CH:71]=[CH:67][CH:68]=[C:69]1[C:59]1[CH:54]=[CH:55][CH:56]=[CH:57][C:58]=1[CH2:53][NH:51][C:49]([C:48]1[CH:64]=[CH:65][C:45]([CH2:44][NH:43][C:32]([N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[N:11]([CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[C:12](=[O:22])[CH2:13]2)=[O:33])=[C:46]([CH3:66])[CH:47]=1)=[O:50]Participants
7
Reactant 6
Product 1
Procedure
A solution of 1-[2-(tert-butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example 21E (110 mg, 0.34 mmol) and diisopropylethylamine (77 μl, 0.44 mmol) in THF (8.0 ml) and a solution of phosgene in toluene (20%, 233 μl, 0.44 mmol) were stirred together for 2 h. A solution of 4-aminomethyl-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide from Example 21D (108 mg, 0.34 mmol) and diisopropylethylamine (77 μl, 0.44 mmol) in THF (5.0 ml) was added and the mixture was stirred for 18 h and evaporated in vacuo. The residue was directly in the next step of the synthesis as described in Example 21G.
Workup
- customevaporated in vacuo
- customThe residue was directly in the next step of the synthesis
Sources & evidence
- ORD record
- ord-2e2e1e3287644e469e75573cdd0329bc
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063038B2
Reaction notes
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