1-Phenylpiperazinium chloride → 5-Bromo-3-nitro-4-(4-phenylpiperazin-1-yl)pyridin-2-amine

HRID 416768Notes

Reaction equation

HRID 416768 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.Br[C:28]1[C:29](Cl)=[C:30]([N+]([O-])=O)C(N)=N[CH:33]=1.CCN(C(C)C)C(C)C.Cl.C1(N2CCNCC2)C=CC=CC=1>C(O)(C)C>[Br:26][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:30]=[CH:29][CH:28]=[CH:33][CH:18]=3)[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 751641-Phenylpiperazinium chlorideHCID 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 468683475-Bromo-3-nitro-4-(4-phenylpiperazin-1-yl)pyridin-2-amineYield 91%

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 (3.5 eq, 4.16 mmol, 0.72 mL), isopropanol (7 mL) and 1-phenylpiperazine hydrochloride (1.1 eq, 1.31 mmol, 260 mg). After 18 h the precipitate was filtered and washed with cold water (2×3 mL) to give the product (407 mg, 91%) as an orange solid; 1H-NMR (500 MHz, DMSO-d6) 3.20 (br s, 4H, piperazine N(CH2)2), 3.30 (hidden by DMSO peak, 4H, piperazine N(CH2)2), 6.83 (t, J=7.5 Hz, 1H, phenyl H-4), 6.98 (d, J=8.4 Hz, 2H, phenyl H-2 & H-6), 7.04 (br s, 2H, NH2), 7.25 (t, J=7.9 Hz, 2H, phenyl H-3 & H-5), 8.21 (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-78a9b256e24c4b6d8c77b19dd30e74f1
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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