1-Methylpiperazine → HCID 86711950, compound

HRID 1475258Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:13]([CH3:14])=[N:12][C:11]([C:15]3[O:16][C:17]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=4)=[CH:18][N:19]=3)=[N:10]2)[CH:5]=[CH:4][N:3]=1.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CS(C)=O>[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([C:2]2[CH:7]=[C:6]([CH2:8][N:9]3[C:13]([CH3:14])=[N:12][C:11]([C:15]4[O:16][C:17]([C:20]5[CH:21]=[CH:22][C:23]([O:26][C:27]([F:30])([F:28])[F:29])=[CH:24][CH:25]=5)=[CH:18][N:19]=4)=[N:10]3)[CH:5]=[CH:4][N:3]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-(1-((2-chloropyridin-4-yl)methyl)-5-methyl-1H-1,2,4-triazol-3-yl)-5-(4-(trifluoromethoxy)phenyl)oxazole (60 mg, 0.14 mmol) and 1-methyl-piperazine (1 mL) in DMSO (2 mL) was stirred at 140° C. for 16 h under Ar atmosphere. The mixture was then cooled to RT, and purified by prep-HPLC (Mobile phase: A=0.1% TFA/H2O, B=MeCN; Gradient: B=5%-95% in 8 min; Column: XBridge C18, 5 um, 30 mm×150 mm) to afford the title compound a solid. MS (ES+) C24H24F3N7O2 requires: 499. found: 500 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.18 (d, J=5.0 Hz, 1H), 7.80 (d, J=9.0 Hz, 2H), 7.51 (s, 1H), 7.29 (d, J=9.0 Hz, 2H), 6.48 (d, J=5.0 Hz, 1H), 6.38 (s, 1H), 5.32 (s, 2H), 3.62 (m, 4H), 2.67 (m, 4H), 2.50 (s, 3H).

Workup

temperatureThe mixture was then cooled to RT
custompurified by prep-HPLC (Mobile phase
waitGradient: B=5%-95% in 8 min

Sources & evidence

ORD record: ord-e32df302aa004dce9274c18135852359
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018380B2

Reaction notes

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