Trifluoroacetic acid → 3-(4-(3-(4-fluorophenoxy)azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide

HRID 522893Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)[CH:5]=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([NH:26][CH3:27])=[O:25].FC(F)(F)C(O)=O>CC(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([NH:26][CH3:27])=[O:25])[CH:7]=3)[CH2:9]2)=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 92 °C

Procedure

To 2-chloro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyridine (90 mg, 0.323 mmol) and 3-amino-N-methylbenzamide (72.7 mg, 0.484 mmol) in 2-propanol (3.00 mL) in a disposable sealed tube at RT was added trifluoroacetic acid, (0.075 mL, 0.969 mmol). The resulting reaction mixture was heated at 84° C. for 5 days and 92° C. for 20 days, cooled to RT, concentrated, purified using MPLC (5 g cartridge, 12 g column, 0 to 100% 90/10 CH2Cl2-MeOH in CH2Cl2) giving 3-(4-(3-(4-fluorophenoxy)azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide (73.6 mg).

Workup

customThe resulting reaction mixture
temperaturecooled to RT
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-e2be3ed11a494a2e9f9dd35990228af4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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