Hydrochloric Acid → (1S,2S)-2-(6-tert-butyl-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexanecarboxylic acid
Reaction equation
[C:1]([C:5]1[C:10]([F:11])=[C:9](S(C)=O)[N:8]=[C:7]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[NH:17][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:25][C@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@@H:27]1[C:32]([OH:34])=[O:33].C([O-])([O-])=O.[Na+].[Na+].CCN(C(C)C)C(C)C.Cl>C1COCC1.CC#N>[C:1]([C:5]1[N:6]=[C:7]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[NH:17][CH:16]=2)[N:8]=[C:9]([NH:25][C@H:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C@@H:27]2[C:32]([OH:34])=[O:33])[C:10]=1[F:11])([CH3:4])([CH3:3])[CH3:2]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 3-(tert-butyl-5-fluoro-6-(methylsulfinyl)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine, 40c, (0.05 g, 0.14 mmol), (1S,2S)-2-amino-cyclohexanecarboxylic acid (0.04 g, 0.27 mmol), freshly ground Na2CO3 (0.04 g, 0.41 mmol), and iPr2NEt (0.37 mL, 0.27 mmol) in THF (1 mL) and CH3CN (0.5 mL) was heated in a sealed vessel to 140° C. for 30 minutes under microwave irradiation. The mixture was cooled to room temperature. A solution of 1N HCl (0.5 mL, 0.5 mmol) was added and the mixture was concentrated to give a yellow solid, which was purified by reverse phase HPLC (0%-50% methanol in water) to afford the desired product, 629, as off-white solid.
Workup
- temperatureThe mixture was cooled to room temperature
- concentrationthe mixture was concentrated
- customto give a yellow solid, which
- customwas purified by reverse phase HPLC (0%-50% methanol in water)
Sources & evidence
- ORD record
- ord-18e6fb86f4e446eab7a99ea9e38f828c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829007B2
Reaction notes
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