Hydrochloric Acid → HCID 178461866, compound

HRID 625647Notes

Reaction equation

HRID 625647 reaction equation
Cl.C(OC([NH:9][C@H:10]([C:12]1[NH:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([C:33]4[N:34]=[C:35]([C@@H:38]([NH:40]C(=O)OC(C)(C)C)[CH3:39])[NH:36][CH:37]=4)=[CH:29][CH:28]=2)[CH:21]=[CH:20]3)[N:16]=1)[CH3:11])=O)(C)(C)C>O1CCOCC1.CO>[NH2:9][C@H:10]([C:12]1[NH:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27]2[CH:28]=[CH:29][C:30]([C:33]4[N:34]=[C:35]([C@@H:38]([NH2:40])[CH3:39])[NH:36][CH:37]=4)=[CH:31][CH:32]=2)[CH:21]=[CH:20]3)[N:16]=1)[CH3:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178462196HCID 178462196, compound

Product 1

HCID 178461866HCID 178461866, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4N HCl in dioxane (10 mL) was added to tert-butyl ((1S)-1-(4-(4-(6-(2-((1S)-1-((tert-butoxycarbonyl)amino)ethyl)-1H-imidazol-4-yl)-2-naphthyl)phenyl)-1H-imidazol-2-yl)ethyl)carbamate (368 mg. 0.59 mmol) in MeOH (10 mL) and stirred at ambient conditions for 5 hours, concentrated, and dried under vacuum. Tetra HCl salt (assume theoretical: 334 mg). LC-MS retention time 1.33 min; calcd. for C26H27N6: 423.23 m/z Found 423.17 [M+H]+. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 2 min, a hold time of 1 min and an analysis time of 3 min where Solvent A was 5% methanol/95% water/0.1% TFA and Solvent B was 95% methanol/5% water/0.1% TFA. MS data was determined using a MICROMASS® Platform for LC in electrospray mode.

Workup

  1. concentrationconcentrated
  2. customdried under vacuum
  3. customequipped with a PHENOMENEX® Luna 2.0×30 mm column
  4. washThe elution conditions
  5. customa gradient time of 2 min
  6. customa hold time of 1 min
  7. customan analysis time of 3 min where Solvent A was 5% methanol/95% water/0.1% TFA and Solvent B

Sources & evidence

ORD record
ord-d925e00a9633483eaaaf59a3c1047483
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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