Ethylenediamine → HCID 86643345, compound
Reaction equation
[Cl:1][C:2]1[C:3]([F:33])=[C:4]([C:16]([NH:18][C@@H:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][C@@H:20]2[F:32])=[O:17])[N:5](COCC[Si](C)(C)C)[C:6]=1[CH3:7].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N)CN>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([F:33])=[C:4]([C:16]([NH:18][C@@H:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:21][C@@H:20]2[F:32])=[O:17])[NH:5][C:6]=1[CH3:7]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
tert-butyl (3S,4R)-4-{[(4-chloro-3-fluoro-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidine-1-carboxylate (Intermediate 259, 80 mg, 0.16 mmol) was dissolved in anhydrous THF (6 ml), followed by the addition of tetra-butyl ammonium fluoride (1 ml, 1M in THF) and ethylene diamine (1 mmol), the mixture was then stirred at 50° C. over night. After cooling down to room temperature, the reaction mixture was diluted with ethyl acetate (20 ml) and washed with saturated aqueous sodium bicarbonate (10 ml) and brine (10 ml), dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (100%˜70% hexanes/ethyl acetate) to give the desired product (55 mg).
Workup
- temperatureAfter cooling down to room temperature
- washwashed with saturated aqueous sodium bicarbonate (10 ml) and brine (10 ml)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- custompurified by column chromatography (100%˜70% hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-2a7d1e79844f4d2fbed364af890ca5c4
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399489B2
Reaction notes
Loading…