1-Ethylpiperazine → 5-Bromo-4-(4-ethylpiperazin-1-yl)-3-nitropyridin-2-amine

HRID 416766Notes

Reaction equation

HRID 416766 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18](NC3SC=CN=3)=O)[CH2:13][CH2:12]2)[C:5]([Br:26])=[CH:4][N:3]=1.BrC1C(Cl)=C([N+]([O-])=O)C(N)=NC=1.CCN(C(C)C)C(C)C.C(N1CCNCC1)C>C(O)(C)C>[Br:26][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 468678032-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

Product 1

HCID 578972285-Bromo-4-(4-ethylpiperazin-1-yl)-3-nitropyridin-2-amineYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

This was prepared using the same procedure as for 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide, but here using 5-bromo-4-chloro-3-nitropyridin-2-amine (300 mg, 1.19 mmol), DIPEA (1.1 eq, 1.31 mmol, 0.23 mL), isopropanol (7 mL) and 1-ethylpiperazine (1.1 eq, 1.31 mmol, 0.17 mL). After 18 h the precipitate was filtered and washed with cold water (2×3 mL) to give the product (212 mg, 54%) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.04 (t, J=7.0 Hz, 3H, CH2CH3), 2.46-2.58 (2 m, 6H, CH2CH3 and piperazine N(CH2)2), 3.08 (br s, 4H, piperazine N(CH2)2), 6.98 (br s, 2H, NH2), 8.16 (s, 1H, pyridine H-6);

Workup

  1. customThis was prepared
  2. filtrationAfter 18 h the precipitate was filtered
  3. washwashed with cold water (2×3 mL)

Sources & evidence

ORD record
ord-20b4fe0e89e946c4aece9c3b4f46f4c5
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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