Diisopropylethylamine → 3-((4-(3-(4-chloro-2-fluorophenoxy) azetidin-1-yl)-6-methyl-1,3,5-triazin-2-yl)amino)-N-methylbenzamide

HRID 522920Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])[CH2:9]2)[N:5]=[C:4]([CH3:21])[N:3]=1.CCN(C(C)C)C(C)C.[NH2:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([NH:37][CH3:38])=[O:36]>C(O)(C)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:6]3[N:5]=[C:4]([CH3:21])[N:3]=[C:2]([NH:31][C:32]4[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=4)[C:35]([NH:37][CH3:38])=[O:36])[N:7]=3)[CH2:9]2)=[C:14]([F:20])[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-6-methyl-1,3,5-triazine (1.0 g, 3.04 mmol) in Isopropanol (10 mL) was added DIPEA (0.8 mL) and 3-amino-N-methylbenzamide (0.460 g, 3.04 mmol) and the reaction mixture was stirred at 80° C. for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 mL) and water (2×40 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-((4-(3-(4-chloro-2-fluorophenoxy) azetidin-1-yl)-6-methyl-1,3,5-triazin-2-yl)amino)-N-methylbenzamide (0.057 g, 6%) as a solid. Observed mass (M+1): 443.1.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with EtOAc (2×40 mL) and water (2×40 mL)
washThe organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-eb9ffce00a6c41ed9d9fcd7ec93dfafe
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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