Triethylamine → 3-(1H-benzo[d]imidazol-2-yl)-5-(1-(thiazol-2-yl)-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

HRID 1959410Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:22])=[N:12][CH:13]=[C:14]([C:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH:21]=2)[N:15]=1.C(N(CC)CC)C.Cl[C:31]1[S:32][CH:33]=[CH:34][N:35]=1>CS(C)=O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:22])=[N:12][CH:13]=[C:14]([C:16]2[CH2:17][CH2:18][N:19]([C:31]3[S:32][CH:33]=[CH:34][N:35]=3)[CH2:20][CH:21]=2)[N:15]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of 3-(1H-benzo[d]imidazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine (100 mg, 0.1922 mmol) in DMSO (2.000 mL) was treated with triethylamine (58.35 mg, 80.37 μL, 0.5766 mmol) and 2-chlorothiazole (27.57 mg, 0.2306 mmol) and heated in the microwave for 40 minutes at 160° C. The reaction mixture was filtered and purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound (20.6 mg, 15% Yield). 1H NMR (400.0 MHz, DMSO) d 2.89 (s, 2H), 3.80 (t, J=5.7 Hz, 2H), 4.21 (d, J=2.5 Hz, 2H), 6.86 (s, 1H), 6.94-6.96 (m, 1H), 7.28-7.31 (m, 3H), 7.69 (s, 2H) and 8.41 (s, 1H) ppm; MS (ES+) 376.0

Workup

filtrationThe reaction mixture was filtered
custompurified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
customThe fractions were collected
customfreeze-dried

Sources & evidence

ORD record: ord-5705f52b67b9447a86640e8fcc4223a9
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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