1-(6-Bromonaphthalene-2-sulfonyl)piperazine → HCID 178432520, compound

HRID 1937320Notes

Reaction equation

HRID 1937320 reaction equation
Cl.[CH3:2][C:3]1[NH:4][CH:5]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[N:7]=1.[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([S:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)(=[O:30])=[O:29])[CH:22]=[CH:21]2>C(O)C.CCCCCC>[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([S:28]([N:31]1[CH2:32][CH2:33][N:34]([C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([C:6]4[N:7]=[C:3]([CH3:2])[NH:4][CH:5]=4)=[CH:16][CH:15]=3)[CH2:35][CH2:36]1)(=[O:29])=[O:30])[CH:22]=[CH:21]2

Participants

4

Reactant 2

HCID 223297091-(6-Bromonaphthalene-2-sulfonyl)piperazineHCID 178432525HCID 178432525, compound

Product 1

HCID 178432520HCID 178432520, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

By an exactly analogous method to that described in Example 1, starting from 4-(2-methylimidazol-4-yl)benzoic acid hydrochloride and 1-(6-bromonaphth-2-ylsulphonyl)piperazine was prepared 1-(6-bromonaphth-2-ylsulphonyl)-4-[4-(2-methylimidazol-4-yl)benzoyl]piperazine (423 mg, 85% yield), m.p. 215-216° C. (from ethanol/hexane), 1H NMR (d6DMSO) 2.3 ppm (s,3H), 3.0-3.2 ppm (broad s,4H), 3.4-3.7 ppm (broad s,4H), 7.2 ppm (d,2H), 7.5 ppm (s,1H), 7.7 ppm (d,2H), 7.8 ppm (t,2H), 8.2 ppm (t,2H), 8.4 ppm (s,1H), 8.45 ppm (s,1H), 11.8 ppm (broad s,1H), the spectrum also contained signals due to ethanol (˜0.33 mol eq.); microanalysis, found: C, 55.4; H, 4.8; N, 9.9; S, 5.8%; C25H23N4O3BrS requires: C, 55.6; H, 4.5; N, 10.1; S, 5.8%; MS (M+H)+ 539/541.

Sources & evidence

ORD record
ord-b047de670fc247f79074198c80ac3564
Source dataset
uspto-grants-2002_05
Patent number
US06395731B1

Reaction notes

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