Methanesulfonyl chloride → HCID 86671469, compound
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[N:11]=[C:12]3[N:22]([CH:23]=2)[CH2:21][CH2:20][O:19][C:18]2[C:13]3=[CH:14][C:15]([CH:24]([OH:26])[CH3:25])=[CH:16][CH:17]=2)[N:5]([CH:7]([CH3:9])[CH3:8])[CH:6]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([O:26][CH:24]([C:15]1[CH:14]=[C:13]2[C:18]([O:19][CH2:20][CH2:21][N:22]3[C:12]2=[N:11][C:10]([C:4]2[N:5]([CH:7]([CH3:9])[CH3:8])[CH:6]=[C:2]([CH3:1])[N:3]=2)=[CH:23]3)=[CH:17][CH:16]=1)[CH3:25])(=[O:30])=[O:29]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-{4-[4-methyl-1-(propan-2-yl)-1H-imidazol-2-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethan-1-ol (10 mg, 0.028 mmol) in DCM (2 mL) at 0° C. was added TEA (14 mg, 0.139 mmol) and methanesulfonyl chloride (6.0 mg, 0.053 mmol). The reaction mixture was further stirred at 0° C. for 2 h. TLC showed the reaction was completed. After being quenched with aqueous NaHCO3 (5 mL), the resultant mixture was extracted with DCM (3×5 mL), washed with brine (2×5 mL). The organic phase was dried over Na2SO4 and concentrated to give 1-{4-[4-methyl-1-(propan-2-yl)-1H-imidazol-2-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethyl methanesulfonate (12 mg, 100% yield), which was directly used in the next step without further purification.
Workup
- customAfter being quenched with aqueous NaHCO3 (5 mL)
- extractionthe resultant mixture was extracted with DCM (3×5 mL)
- washwashed with brine (2×5 mL)
- dry with materialThe organic phase was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f4a0705101714f23970f649e2916a0dc
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090628B2
Reaction notes
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