Hydrochloric Acid → HCID 178511662, compound

HRID 2088992Notes

Reaction equation

HRID 2088992 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](S(C)(=O)=O)[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.[C@H:30]1([NH2:37])[CH2:35][CH2:34][C@H:33]([NH2:36])[CH2:32][CH2:31]1.C(N(CC)CC)C.[OH-].[Na+].Cl>O1CCOCC1>[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][C@H:33]2[CH2:34][CH2:35][C@H:30]([NH2:37])[CH2:31][CH2:32]2)[N:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 87192404HCID 87192404, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511662HCID 178511662, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 42b (160 mg, 0.356 mmol), trans-cyclohexane-1,4-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 cooled and concentrated in vacuo. The residue was taken into methanol (3 mL), treated with dropwise addition of NaOH solution (1.0 mL, 1.0 mmol), stirred at room temperature for 1 hour, neutralized with dilute hydrochloric acid, and purified by reverse-phase HPLC (same condition as described in Example 7b) to afford the title product (28 mg, 23% yield). MS (ESI+) m/z 343 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 1.33-1.63 (m, 4H) 1.98-2.20 (m, 4H) 2.99-3.15 (m, 1H) 3.73-3.87 (m, 1H) 7.11 (s, 1H) 7.17 (dd, J=7.93, 4.58 Hz, 1H) 7.73 (s, 2H) 8.30 (dd, J=4.58, 1.53 Hz, 1H) 8.36 (s, 1H) 8.78 (d, J=7.93 Hz, 1H) 12.05 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. custompurified by reverse-phase HPLC (same condition as described in Example 7b)

Sources & evidence

ORD record
ord-cb0fe4d4a86d466d95f909238b92a225
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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