(Diethylamino)sulfur trifluoride → HCID 67112685, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][N:27]2[CH2:30][C:29](O)([C:31]([O:33][CH3:34])=[O:32])[CH2:28]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.CCN(S(F)(F)[F:42])CC>C(Cl)Cl>[F:42][C:29]1([C:31]([O:33][CH3:34])=[O:32])[CH2:28][N:27]([CH2:26][C:4]2[CH:5]=[CH:6][C:7]([C:8]3[S:9][C:10]4[C:15]([N:16]=3)=[CH:14][CH:13]=[C:12]([C:17]3([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:19][CH2:18]3)[N:11]=4)=[C:2]([F:1])[CH:3]=2)[CH2:30]1Participants
4
Procedure
To a solution of methyl 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-3-hydroxyazetidine-3-carboxylate (0.0334 g, 0.068 mmol) at 0° C. in anhydrous DCM was added 1.0 mL was added DAST (0.011 mL, 0.082 mmol). The reaction mixture was stirred for 10 min. at which time the reaction was quenched carefully with water and extracted with DCM. The organics were dried over magnesium sulfate and concentrate in vacuo. Purification by silica gel afford methyl 3-fluoro-1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate. MS (ESI) m/z: Calculated 491.2; Observed: 492.0 (M++1).