Ethyl Acetate → N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxyazetidin-1-yl)-5-iodonicotinamide

HRID 525766Notes

Reaction equation

[OH:1][CH:2]1[CH2:5][NH:4][CH2:3]1.CCN(C(C)C)C(C)C.Cl[C:16]1[C:35]([I:36])=[CH:34][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([Cl:33])([F:32])[F:31])=[CH:25][CH:24]=2)=[O:21])=[CH:18][N:17]=1.CCOC(C)=O>CC(O)C>[Cl:33][C:30]([F:31])([F:32])[O:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20](=[O:21])[C:19]2[CH:34]=[C:35]([I:36])[C:16]([N:4]3[CH2:5][CH:2]([OH:1])[CH2:3]3)=[N:17][CH:18]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 140 °C

Procedure

3-Hydroxyazetidine (164 mg, 2.18 mmol) and DIPEA (0.419 mL, 2.396 mmol) were added to a suspension of 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (Stage 48.3, 500 mg, 1.089 mmol) in iPrOH (2 mL). and stirred at 140° C. for 16 h. EtOAc (80 mL) was added and the solution was washed with 1 M HCl (30 mL), aq. sat. NaHCO3 solution (30 mL) and water (30 mL), dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the title product as yellow foam. HPLC (Condition 7) tR=6.64 min, UPLC-MS (Condition 3) tR=1.08 min, m/z=496.0/498.0 [M+H]+.

Workup

washthe solution was washed with 1 M HCl (30 mL), aq. sat. NaHCO3 solution (30 mL) and water (30 mL)
dry with materialdried over Na2SO4
customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-569f44f37d154022924c3a51556c3a5c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340537B2

Reaction notes

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