Anisole → N-[5-(4-amino-2-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095774Notes

Reaction equation

[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23]C(=O)OC(C)(C)C)=[CH:19][C:18]=2[F:31])[N:10]=3)=[O:5])[CH2:3][CH2:2]1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:11]2[N:10]=[C:9]3[S:8][C:7]([NH:6][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])=[N:15][C:14]3=[CH:13][CH:12]=2)=[C:18]([F:31])[CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl [4-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-3-fluorophenyl]carbamate (0.50 g, 1.12 mmol) in trifluoroacetic acid (10 mL) was added anisole (0.5 mL), and the mixture was stirred at 0° C. for 2 hr. Trifluoroacetic acid was evaporated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogen carbonate and saturated brine in this order, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/9) to give the title compound (294 mg, 76%) as a white solid.

Workup

customTrifluoroacetic acid was evaporated under reduced pressure, ethyl acetate
additionwas added to the residue
washthe mixture was washed with saturated aqueous sodium hydrogen carbonate and saturated brine in this order
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/9)

Sources & evidence

ORD record: ord-ab58f47b61464c45b9455f75435bc578
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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