5-Bromo-4-chloro-3-nitropyridin-2-amine → HCID 57897270, compound

HRID 416899Notes

Reaction equation

HRID 416899 reaction equation
[N:1]1([CH2:7][C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Br:13][C:14]1[C:15](Cl)=[C:16]([N+:21]([O-:23])=[O:22])[C:17]([NH2:20])=[N:18][CH:19]=1>CC(O)C.CCN(C(C)C)C(C)C>[Br:13][C:14]1[C:15]([N:4]2[CH2:3][CH2:2][N:1]([CH2:7][C:8]3[S:9][CH:10]=[CH:11][N:12]=3)[CH2:6][CH2:5]2)=[C:16]([N+:21]([O-:23])=[O:22])[C:17]([NH2:20])=[N:18][CH:19]=1

Participants

5

Reactant 2

HCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 534404461-[(1,3-Thiazol-2-yl)methyl]piperazine

Product 1

HCID 57897270HCID 57897270, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
65 °C

Procedure

The resulting 2-(piperazin-1-ylmethyl)thiazole (supposedly 0.580 g, 3.18 mmol, 1 eq) was suspended in iPrOH (3.1 mL) and DIPEA (2.2 mL). To this solution, 5-bromo-4-chloro-3-nitropyridin-2-amine (0.800 g, 3.18 mmol, 1 eq) was added and the reaction mixture was heated and stirred for 17 h at 65° C. The mixture was filtered, washed with iPrOH (3×3 mL), Et2O (2×3 mL) and dried to give the title compound as a bright yellow powder (0.750 g, 59%); 1H-NMR (500 MHz, DMSO-d6): δ 2.65 (br s, 4H, piperazine N(CH2)2), 3.09 (m, 4H, piperazine N(CH2)2), 3.90 (s, 2H, NCH2), 6.98 (s, 2H, NH2), 7.66 (d, J=3.0 Hz, 1H, thiazole 5-H), 7.72 (d, J=3.0 Hz, 1H, thiazole 4-H), 8.16 (s, 1H, pyridine 6-H); LC (Method B)-MS (ESI, m/z): Rt=2.90 mins-399/401 [(M+H+), Br isotopic pattern, 100%].

Workup

  1. temperaturethe reaction mixture was heated
  2. filtrationThe mixture was filtered
  3. washwashed with iPrOH (3×3 mL), Et2O (2×3 mL)
  4. customdried

Sources & evidence

ORD record
ord-ec91e2c2cde244729cf3039c4e2fb6db
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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