Hydrochloric Acid → Ammonium Acetate

HRID 2089059Notes

Reaction equation

HRID 2089059 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](S(C)(=O)=[O:9])[N:5]=[C:4]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14](S(C3C=CC=CC=3)(=O)=O)[CH:13]=2)[CH:3]=1.[CH:30]1([NH2:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[NH2:36].C(N(CC)CC)C.[OH-:45].[Na+].Cl>O1CCOCC1>[C:35]([O-:9])(=[O:45])[CH3:30].[NH4+:5].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[N:5]=[C:6]([NH:36][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH:30]2[NH2:37])[N:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 46101,2-DiaminocyclohexaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 87192404HCID 87192404, compound

Product 2

HCID 517165Ammonium AcetateHCID 49830315HCID 49830315, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 42b (160 mg, 0.356 mmol), cyclohexane-1,2-diamine (81 mg, 0.713 mmol), triethylamine (0.10 ml, 0.713 mmol) and dioxane (4 ml) was heated at 60° C. for 2 hours. The reaction mixture was concentrated in vacuo. To a mixture of the residue in methanol (10 mL) was added dropwise NaOH solution (1.43 ml, 1.43 mmol). The mixture was stirred at room temperature for 40 minutes. The reaction mixture was neutralized with dilute hydrochloric acid and purified by reverse-phase HPLC performed on a Phenomenex Luna C8 AXIA column (30×75 mm, 100 Å) using a gradient of 10% to 95% acetonitrile: 10 mM ammonium acetate in water over 12 minutes at a flow rate of 50 mL/minutes to give the title compound. MS (ESI) m/e 343 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 1.13-1.43 (m, 4H) 1.55-1.77 (m, 4H) 2.03-2.14 (m, 1H) 2.62-2.71 (m, 1H) 6.98-7.06 (m, 1H) 7.06-7.11 (m, 1H) 7.15-7.21 (m, 1H) 8.28 (dd, J=4.73, 1.68 Hz, 1H) 8.32-8.37 (m, 1H) 8.74-8.85 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo a mixture of the residue in methanol (10 mL)
  3. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-ed5fa964867f40cca88116ed365c8d9a
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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