Hydrochloric Acid → HCID 67001443, compound

HRID 2279239Notes

Reaction equation

HRID 2279239 reaction equation
Cl.[CH:2]1([C:5]([N:7]2[CH2:13][CH2:12][CH:11]3[CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH2:17][N:10]3[C:9]3[N:25]=[CH:26][CH:27]=[CH:28][C:8]2=3)=[O:6])[CH2:4][CH2:3]1>C(Cl)Cl>[CH:2]1([C:5]([N:7]2[CH2:13][CH2:12][CH:11]3[CH2:14][NH:15][CH2:16][CH2:17][N:10]3[C:9]3[N:25]=[CH:26][CH:27]=[CH:28][C:8]2=3)=[O:6])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67001731HCID 67001731, compound

Product 1

HCID 67001443HCID 67001443, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of HCl (4 M in dioxane, 250 μl, 1 mmol) was added to a solution of the product of Example 72B (26.3 mg, 0.071 mmol) in CH2Cl2 (1.3 mL), and the mixture was stirred at room temperature for 70 hours. The mixture was concentrated under vacuum, and the residue was crystallized from ethyl acetate-ethanol (4 mL, 2:1) to provide the title compound as the bis-hydrochloride salt: 1H NMR (400 MHz, pyridine-d5, 110° C.) δ ppm 0.41 (dd, J=7.8, 3.5 Hz, 2H), 0.85-0.97 (m, 2H), 1.06-1.21 (m, 1H), 1.51-1.64 (m, 1H), 1.66-1.77 (m, 1H), 2.91 (t, J=11.0 Hz, 1H), 3.25-3.45 (m, 3H), 3.53-4.09 (m, 5H), 6.77 (dd, J=7.6, 4.9 Hz, 1H), 7.37 (dd, J=7.6, 1.5 Hz, 1H), 8.16 (dd, J=4.6, 1.5 Hz, 1H); MS (DCI) m/z 273 (M+H)+. Elemental analysis is calculated for C15H20N4O.2HCl.0.5H2O.0.4 EtOAc: C, 51.19; H, 6.78; N, 14.38. Found: C, 51.23; H, 6.57; N, 14.12.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was crystallized from ethyl acetate-ethanol (4 mL, 2:1)

Sources & evidence

ORD record
ord-8b927db0e9f749f1ad8506afc11ee2a7
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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