Pyridine → phenyl N-[4-[[2-(cyclopropanecarbonylamino)-4-pyridyl]oxy]-2-fluoro-phenyl]carbamate

HRID 2200119Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][C:3]=1[F:21].N1C=CC=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30].CCOC(C)=O>C(Cl)Cl>[CH:16]1([C:14]([NH:13][C:9]2[CH:8]=[C:7]([O:6][C:5]3[CH:19]=[CH:20][C:2]([NH:1][C:29](=[O:30])[O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:3]([F:21])[CH:4]=3)[CH:12]=[CH:11][N:10]=2)=[O:15])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 2.5 °C

Procedure

Mix N-[4-(4-amino-3-fluoro-phenoxy)-2-pyridyl]cyclopropanecarboxamide (500 mg, 1.7 mmol), DCM (8 mL) and pyridine (345 mg) and cool to 0-5° C. Add a solution of phenyl chloroformate (350 mg, 2.2 mmol) in DCM (1 mL). Stir the reaction at room temperature for 1.5 hrs. TLC (EtOAc:PE=1;1) shows the reaction is complete. Quench the reaction with water (5 mL). Wash the organic layer with 1N HCl solution, saturated NaHCO3 solution and brine respectively. Dry the organic layer with anhydrous Na2SO4. Filter and concentrate to give the crude product (710 mg) which is used without further purification. MS: (M+1): 408.

Workup

customthe reaction at room temperature for 1.5 hrs
customQuench
customthe reaction with water (5 mL)
washWash the organic layer with 1N HCl solution, saturated NaHCO3 solution and brine respectively
dry with materialDry the organic layer with anhydrous Na2SO4
filtrationFilter
concentrationconcentrate

Sources & evidence

ORD record: ord-276437ebb30d45d288d7e17b266aed5d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359338B2

Reaction notes

Loading…