Diisopropylethylamine → HCID 53372734, compound

HRID 522930Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH2:36][C:37]1[C:38]([CH3:47])=[C:39]([CH:44]=[CH:45][CH:46]=1)[C:40]([NH:42][CH3:43])=[O:41]>C(O)(C)C>[CH3:43][NH:42][C:40](=[O:41])[C:39]1[CH:44]=[CH:45][CH:46]=[C:37]([NH:36][C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=4)[CH2:10][CH2:9]3)[N:5]=[CH:4][N:3]=2)[C:38]=1[CH3:47]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-4-(4-((4-(trifluoromethoxy)benzyl)oxy)piperidin-1-yl)-1,3,5-triazine (500 mg, 1.28 mmol) in isopropanol (4 mL, 3 mL/mmol) was added DIPEA (0.4 mL, 1.92 mmol) and 3-amino-N,2-dimethylbenzamide (211 mg, 1.29 mmol) and the reaction was stirred at 80° C. for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×30 ml). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided N,2-dimethyl-3-((4-(4-((4-(trifluoromethoxy)benzyl)oxy)piperidin-1-yl)-1,3,5-triazin-2-yl)amino)benzamide (100 mg, 16%) as a solid. Observed mass (M+1): 517.1.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with EtOAc (2×30 ml)
washThe organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-169db329ec154394a3279adb778b6745
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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