1-(Methylsulfonyl)piperazine → 5-Bromo-4-(4-(methylsulfonyl)piperazin-1-yl)-3-nitropyridin-2-amine

HRID 416770Notes

Reaction equation

HRID 416770 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](CC(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.[CH3:39][S:40](N1CCNCC1)(=[O:42])=[O:41]>C(O)(C)C>[Br:26][C:5]1[C:6]([N:11]2[CH2:12][CH2:13][N:14]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:15][CH2:16]2)=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 7091611-(Methylsulfonyl)piperazineHCID 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 578973105-Bromo-4-(4-(methylsulfonyl)piperazin-1-yl)-3-nitropyridin-2-amineYield 34%

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 (200 mg, 0.79 mmol), isopropanol (12 mL) and 1-methanesulfonylpiperazine (1.1 eq, 0.87 mmol, 143 mg). After 18 h the precipitate was filtered and washed with cold water (2×3 mL) to give the product (101 mg, 34%) as an orange solid; δH (500 MHz, DMSO-d6) 2.94 (s, 3H, CH3), 3.12 (s, br, 4H, piperazine N(CH2)2), 3.25 (s, br, 4H, piperazine N(CH2)2), 7.06 (s, br, 2H, NH2), 8.22 (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-14f52f8e20fd4419ad8393c77ccf9c2d
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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