Hydrochloric Acid → HCID 67001443, compound

HRID 1186244Notes

Reaction equation

HRID 1186244 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.2 HCl.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-9119926feec54c5db2d1bb1179ddeaab
Source dataset
uspto-grants-2014_03
Patent number
US08673896B2

Reaction notes

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