Piperidine → 5-(2-hydroxy-3-morpholinopropyl)-3-methyl-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one
Reaction equation
[OH:1][C@@H:2]([CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH2:3][N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:11][C:12](C=O)=[C:13]([CH3:14])[C:6]=2[C:5]1=[O:17].N1CCCCC1>C(O)C>[OH:1][CH:2]([CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH2:3][N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:11][CH:12]=[C:13]([CH3:14])[C:6]=2[C:5]1=[O:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 78f (50 mg, 0.149 mmol) was dissolved in 261 μl of ethanol under stirring, and added with 5-fluoro-1,3-dihyrdro-indole-2-one (20.28 mg, 0.134 mmol) and piperidine (7.3 μl, 0.074 mmol) to the solution at room temperature. Upon the completion of the addition, the reaction mixture was stirred for 2 hours in dark at 80° C. in an oil bath. After thin lay chromatography showed the disappearance of starting materials, the reaction was stopped, and the oil bath was removed. The reaction system was cooled to room temperature, the reaction solution was filtered and the filter cake was dried to obtain the title compound (S,Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 78(40 mg, yield 57%) as a yellow solid.
Workup
- additionUpon the completion of the addition
- stirringthe reaction mixture was stirred for 2 hours in dark at 80° C. in an oil bath
- customthe oil bath was removed
- filtrationthe reaction solution was filtered
- customthe filter cake was dried
Sources & evidence
- ORD record
- ord-56a062fe97484193880b674bee510b2d
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329682B2
Reaction notes
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