Hydrochloric Acid → 12-(4-Chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene

HRID 2354890Notes

Reaction equation

HRID 2354890 reaction equation
C(OC([N:8]1[CH2:18][CH:17]2[N:19]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:10]([CH2:11][C:12]3[NH:13][N:14]=[CH:15][C:16]=32)[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([N:19]2[CH:10]3[CH2:9][NH:8][CH2:18][CH:17]2[C:16]2[CH:15]=[N:14][NH:13][C:12]=2[CH2:11]3)(=[O:21])=[O:22])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45487090Tert-butyl 12-(4-chlorophenyl)sulfonyl-4,5,10,12-tetrazatricyclo[6.3.1.02,6]dodeca-2(6),3-diene-10-carboxylate

Product 1

HCID 1604539412-(4-Chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12-(4-Chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-10-carboxylic acid tert-butyl ester (207 mg, 0.471 mmol) was covered with HCl in dioxane (4 N, 2 mL). The reaction mixture was stirred at room temperature for 2 h after which it was concentrated under vacuum and purified by preparative HPLC to give 12-(4-chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene as a white solid. Retention time (min)=1.125, method [1], MS (ESI) 339.1 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.59 (d, J=8.2 Hz, 2H), 7.30-7.25 (m, 3H), 5.09 (s, 1H), 4.35-4.14 (m, 1H), 3.25-3.18 (m, 2H), 2.98 (d, J=13.7 Hz, 1H), 2.77 (dd, J=17.0, 7.1 Hz, 2H), 2.55 (d, J=17.0 Hz, 1H)

Workup

  1. concentrationwas concentrated under vacuum
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9d3b117d09bf4a4d80a4e3ae3dad97b6
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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