Methanesulfonyl chloride → HCID 58049436, compound
Reaction equation
[C:1]([NH:11][C:12]1([CH2:15][OH:16])[CH2:14][CH2:13]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN(C(C)C)C(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[C:1]([NH:11][C:12]1([CH2:15][O:16][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:13][CH2:14]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-CBZ-amino-1-(hydroxymethyl)cyclopropane (similarly prepared according to JMC 31, 2004, 1998) (250 mg) was dissolved into DCM (25 ml) with DIPEA (250 l) and stirred at 0° C. for 15 minutes. To the reaction was added MsCl (1.1 eq) and stirred for 30 minutes. The reaction was washed with NaHCO3 solution, water, brine and dried with Na2SO4. The solution was evaporated to give N-CBZ-amino-1-(methylsulfonyloxymethyl)cyclopropane as an off white solid. This solid was mixed with above 6-(7-hydroxy-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide and Cs2CO3 (250 mg) in DMA (4 ml). The reaction was heated at 100° C. for 10 hours and mixed with EtOAc and water, then filtered, further extracted with EtOAc. The combined organic layer was evaporated and purified with silica gel column to give the titled product. Mass: (M+1), 578
Workup
- stirringstirred for 30 minutes
- washThe reaction was washed with NaHCO3 solution, water, brine
- dry with materialdried with Na2SO4
- customThe solution was evaporated
Sources & evidence
- ORD record
- ord-13e46f1cb61f4390b44b68ec50dd82ed
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163923B2
Reaction notes
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