Diisopropylethylamine → HCID 24784535, compound
Reaction equation
C(N(CC)C(C)C)(C)C.Cl[C:11](Cl)([O:13][C:14](=[O:20])OC(Cl)(Cl)Cl)Cl.[F:22][C:23]1[CH:30]=[C:29]([C:31]2[N:32]=[C:33]([NH:36][C:37](C)([CH3:40])[CH2:38]O)[S:34][CH:35]=2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>C(Cl)Cl>[CH3:38][C:37]1([CH3:40])[CH2:11][O:13][C:14](=[O:20])[N:36]1[C:33]1[S:34][CH:35]=[C:31]([C:29]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([F:22])[CH:30]=2)[N:32]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N,N-diisopropylethylamine (1.4 mL, 7.9 mmol) and triphosgene (1.2 g, 3.9 mmol) in 20 mL of dry methylene chloride were added to a solution of 2-fluoro-4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (955 mg, 3.3 mmol), prepared in the previous step, in 50 mL of dry methylene chloride at 0° C. The reaction was stirred at 0° C. for 3 h and then allowed to warm to room temperature. The reaction was washed with 1×100 mL of 2N HCl. The aqueous layer was extracted with methylene chloride (2×100 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give 1.0 g of a yellow solid. Purification of the solid on silica gel using a stepwise gradient of 5% to 40% ethyl acetate-hexane gave the title compound (450 mg, 43%) as a yellow solid, mp 204-206° C.
Workup
- temperatureto warm to room temperature
- washThe reaction was washed with 1×100 mL of 2N HCl
- extractionThe aqueous layer was extracted with methylene chloride (2×100 mL)
- dry with materialThe combined organic layers were dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4998d1dbc4894a6597fdfad80cbd5fb0
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652018B2
Reaction notes
Loading…