Hydrochloric Acid → HCID 178421460, compound

HRID 1471198Notes

Reaction equation

HRID 1471198 reaction equation
Cl.C(OC([N:9]1[C@H:14]([C:15]2[NH:16][CH:17]=[C:18]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[CH:26]=[C:25]([C:30]3[CH:35]=[CH:34][C:33]([C:36]5[N:37]=[C:38]([C@@H:41]6[CH2:46][C@@:45]7([CH3:47])[C@H:43]([CH2:44]7)[N:42]6C(OC(C)(C)C)=O)[NH:39][CH:40]=5)=[CH:32][CH:31]=3)[CH:24]=[CH:23]4)[N:19]=2)[CH2:13][C@@:12]2([CH3:55])[C@@H:10]1[CH2:11]2)=O)(C)(C)C>O1CCOCC1.CO>[CH3:47][C@@:45]12[CH2:44][C@@H:43]1[NH:42][C@H:41]([C:38]1[NH:39][CH:40]=[C:36]([C:33]3[CH:34]=[CH:35][C:30]([C:25]4[CH:24]=[CH:23][C:22]5[C:27](=[CH:28][CH:29]=[C:20]([C:18]6[N:19]=[C:15]([C@@H:14]7[CH2:13][C@@:12]8([CH3:55])[C@H:10]([CH2:11]8)[NH:9]7)[NH:16][CH:17]=6)[CH:21]=5)[CH:26]=4)=[CH:31][CH:32]=3)[N:37]=1)[CH2:46]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178452508HCID 178452508, compound

Product 1

HCID 178421460HCID 178421460, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4N HCl in dioxane (15 mL) was added to tert-butyl(1S,3S,5S)-3-(4-(4-(6-(2-((1S,3S,5S)-2-(tert-butoxycarbonyl)-5-methyl-2-azabicyclo[3.1.0]hex-3-yl)-1H-imidazol-4-yl)-2-naphthyl)phenyl)-1H-imidazol-2-yl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate (250 mg. 0.344 mmol) in MeOH (5 mL) and stirred at ambient conditions for 2 hours, concentrated, and dried under vacuum. Tetra HCl salt (assume theoretical: 231 mg). LC-MS retention time 3.09 min; Calcd. for C34H35N6: 527.29 m/z Found 527.35 [M+H]+. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® 2.0×50 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 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min and an analysis time of 5 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® 2.0×50 mm column
  4. washThe elution conditions
  5. customa gradient time of 4 min
  6. customa hold time of 1 min
  7. customan analysis time of 5 min where Solvent A was 5% methanol/95% water/0.1% TFA and Solvent B

Sources & evidence

ORD record
ord-eb036f26ba98461cb1e488b43d9b4c61
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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