Hydrochloric Acid → HCID 178461866, compound

HRID 1471195Notes

Reaction equation

HRID 1471195 reaction equation
Cl.C(OC(=O)[NH:8][C@H:9]([C:11]1[NH:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:32]5[N:33]=[C:34]([C@@H:37]([NH:39]C(OC(C)(C)C)=O)[CH3:38])[NH:35][CH:36]=5)[CH:28]=4)[CH:23]=3)=[CH:18][CH:17]=2)[N:15]=1)[CH3:10])(C)(C)C>O1CCOCC1.CO>[NH2:39][C@H:37]([C:34]1[NH:35][CH:36]=[C:32]([C:27]2[CH:28]=[C:29]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:14]4[N:15]=[C:11]([C@@H:9]([NH2:8])[CH3:10])[NH:12][CH:13]=4)=[CH:21][CH:20]=2)[CH:31]=[CH:30]3)[N:33]=1)[CH3:38]

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-3346b693462e49ae8f60c7db89376101
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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