1-((2-Methyl-1,3-thiazol-4-yl)methyl)piperazine → 5-Bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

HRID 416885Notes

Reaction equation

[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[N:6]=1.[Br:14][C:15]1[C:16](Cl)=[C:17]([N+:22]([O-:24])=[O:23])[C:18]([NH2:21])=[N:19][CH:20]=1>CC(O)C.CCN(C(C)C)C(C)C>[Br:14][C:15]1[C:16]([N:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:5]3[N:6]=[C:2]([CH3:1])[S:3][CH:4]=3)[CH2:13][CH2:12]2)=[C:17]([N+:22]([O-:24])=[O:23])[C:18]([NH2:21])=[N:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

LC (Method B)-MS (ESI, m/z): Rt=0.50 min—198 [(M+H)+, 100%]. Half of this material (i.e. 2-methyl-4-(piperazin-1-ylmethyl)thiazole; supposedly 0.331 g, 1.68 mmol, 0.55 eq) was suspended in iPrOH (3.3 mL) and DIPEA (1.3 mL). To this solution, 5-bromo-4-chloro-3-nitropyridin-2-amine (0.390 g, 1.53 mmol, 0.45 eq) was added and the mixture heated and stirred for 17 h at 60° C. The mixture was filtered, washed with iPrOH (3×3 mL), cold H2O (3×3 mL), Et2O (2×3 mL), and dried to give the title compound (0.380 g, 55%); 1H-NMR (500 MHz, DMSO-d6): δ 2.50-2.70 (m, 7H, piperazine N(CH2)2 and Me), 3.07 (br s, 4H, piperazine N(CH2)2), 3.60 (s, 2H, NCH2), 6.98 (br s, 2H, NH2), 7.29 (s, 1H. thiazole 5-H), 8.17 (s, 1H, pyridine 6-H); LC (Method B)-MS (ESI, m/z): Rt-2.00 min—413/415 [(M+H+), Br isotopic pattern, 100%].

Workup

temperaturethe mixture heated
filtrationThe mixture was filtered
washwashed with iPrOH (3×3 mL), cold H2O (3×3 mL), Et2O (2×3 mL)
customdried

Sources & evidence

ORD record: ord-180343a1991843de9a985ff4db9df449
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

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