Hydrochloric Acid → 1-(6-Bromonaphth-2-ylsulphonyl)-4-[4-(2-aminoimidazol4-yl)benzoyl]piperazine

HRID 1937321Notes

Reaction equation

HRID 1937321 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:41])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[N:29]=[C:30]([NH:33]C(OC(C)(C)C)=O)[NH:31][CH:32]=4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.Cl>ClCCl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:41])[C:22]3[CH:23]=[CH:24][C:25]([C:28]4[N:29]=[C:30]([NH2:33])[NH:31][CH:32]=4)=[CH:26][CH:27]=3)[CH2:19][CH2:20]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178452975HCID 178452975, compound

Product 1

HCID 1785082971-(6-Bromonaphth-2-ylsulphonyl)-4-[4-(2-aminoimidazol4-yl)benzoyl]piperazineYield 82.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1-(6-bromonaphth-2-ylsulphonyl)-4-[4-(2-t-butyloxycarbonylaminoimidazol-4-yl)benzoyl]piperazine (174 mg, 0.27 mmol) in dichloromethane (1 ml) and dioxan (4 ml) was treated with a solution of hydrogen chloride in dioxan (4 ml of 4M) and stirred overnight. The resulting solid was isolated by filtration to give crude product (163 mg); this was crystallised from ethanol to give 1-(6-bromonaphth-2-ylsulphonyl)-4-[4-(2-aminoimidazol4-yl)benzoyl]piperazine (120 mg, 77% yield), m.p. 274-275° C., 1H NMR (d6DMSO) 3.0-3.1 ppm (broad s,4H), 3.3-3.7 ppm (broad s,4H), 7.35 ppm (d,2H), 7.45 ppm (s,3H), 7.65 ppm (d,2H), 7.8 ppm (t,2H), 8.2 ppm (t,2H), 8.4 ppm (s,1H), 8.45 ppm (s,1H); microanalysis, found: C, 48.8; H, 4.1; N, 11.8; S, 5.5%; C24H22N5O3BrS. 1.0 HCl. 0.5 H2O requires: C, 49.2; H, 4.1; N, 12.0; S, 5.5%; MS (M+H)+ 540/542.

Workup

  1. customThe resulting solid was isolated by filtration
  2. customto give crude product (163 mg)
  3. customthis was crystallised from ethanol

Sources & evidence

ORD record
ord-f695a55ccb764227897138ca7ea160fa
Source dataset
uspto-grants-2002_05
Patent number
US06395731B1

Reaction notes

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