Water → {2-Chloro-4-[(2-{2-[(tetrahydrofuran-2-ylmethyl)amino]ethyl}phenyl)amino]phenyl}(2-methylphenyl)methanone
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16]O)[CH:5]=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[O:19].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH2:38].[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][NH:39][CH2:40][CH:41]2[CH2:42][CH2:43][CH2:44][O:38]2)[CH:5]=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[O:19]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Compound 102 (0.15 g, 0.41 mmol) was dissolved in pyridine (0.2 mL) at 0° C., and p-toluenesulfonyl chloride (0.086 g, 0.45 mmol) was added. The suspension was stirred for 45 min at 0° C., after which the amine (tetrahydro-furfuryl amine, 0.127 mL, 1.23 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. H2O (10 mL) was added and the aqueous phase was extracted with EtOAc (5×10 mL). The combined organic phases were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography using EtOAc/MeOH/Et3N 10:1:0.1 as the eluent to afford the title compound as a yellow oil.
Workup
- stirringThe reaction mixture was stirred at room temperature for 18 h
- extractionthe aqueous phase was extracted with EtOAc (5×10 mL)
- washThe combined organic phases were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated in vacuo
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-3de2afd6be3f4f7199853838712ef4c9
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07034015B2
Reaction notes
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