Diisopropylethylamine → HCID 25140035, compound
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[CH3:19][N:20]([CH3:33])[CH2:21][CH2:22][C@@H:23]([NH2:32])[CH2:24][S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[CH3:33][N:20]([CH3:19])[CH2:21][CH2:22][C@@H:23]([NH:32][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[CH2:24][S:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1Participants
5
Procedure
A solution of 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide (685 mg, 2.3 mmol), (R)—N1,N1-dimethyl-4-phenylsulfanyl-butane-1,3-diamine (500 mg, 2.3 mmol), and DIPEA (0.78 mL, 4.5 mmol) in DMA (18.8 mL) was heated to 100° C. for 6 hours. The reaction was cooled to room temperature and diluted with EtOAc/heptanes (1:1, 50 mL). This solution was washed with water, the layers were separated, and the aqueous layer was extracted with EtOAc/heptanes (1:1) (50 mL×3). The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated to afford the title compound as a yellow solid (965 mg, 82% yield). MS (ESI) m/e (M+H+): 512.2
Workup
- washThis solution was washed with water
- customthe layers were separated
- extractionthe aqueous layer was extracted with EtOAc/heptanes (1:1) (50 mL×3)
- washThe combined organic layers were washed with water and brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-826f450eaab9457db3ae69889b3c9a48
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809352B2
Reaction notes
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