Ethanamine, 2,2,2-trifluoro- → HCID 89967335, compound
Reaction equation
O1CCOCC1.[F:7][C:8]([F:12])([F:11])[CH2:9][NH2:10].CCN(C(C)C)C(C)C.Cl[S:23]([CH2:26][CH2:27][NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:25])=[O:24]>C(#N)C>[F:7][C:8]([F:12])([F:11])[CH2:9][NH:10][S:23]([CH2:26][CH2:27][NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:25])=[O:24]Participants
Procedure
To a dioxane (1 mL) solution of 2,2,2-trifluoroethanamine (80 mg, 0.81 mmol) and DIEA (0.28 mL, 1.6 mmol) at 0° C. was added benzyl (2-(chlorosulfonyl)ethyl)carbamate (150 mg, 0.54 mmol) in acetonitrile (1 mL). The reaction was allowed to reach room temperature over a period of 20 minutes. The reaction mixture was concentrated under reduced pressure, and the residue purified using reverse phase HPLC (YMC Sunfire 5u (C18) 30×100 mm, 0-100% ACN (90% in H2O, 0.1% TFA) using gradient over 16 min with flow rate 40 mL/min and UV detection at 220 nm) to give Compound B30a (95 mg, 39% yield). HPLC: RT=3.84 (LCMS Method M). MS (ES): m/z=340.9 [M+H]+. 1H NMR (500 MHz, CHLOROFORM-d) d 7.43-7.34 (m, 5H), 5.28 (br. s., 2H), 5.15 (s, 2H), 3.86-3.68 (m, 4H), 3.35-3.24 (m, 2H).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue purified
- customphase HPLC (YMC Sunfire 5u (C18) 30×100 mm, 0-100% ACN (90% in H2O, 0.1% TFA) using gradient over 16 min with flow rate 40 mL/min and UV detection at 220 nm)
- customto give Compound B30a (95 mg, 39% yield)
- customRT=3.84 (LCMS Method M)
Sources & evidence
- ORD record
- ord-3cfb5d9d3e1c41ad9174fb5dc8294c50
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987314B2
Reaction notes
Loading…