Hydrochloric Acid → HCID 178461568, compound

HRID 1471197Notes

Reaction equation

HRID 1471197 reaction equation
Cl.C(OC([N:9]1[CH2:13][C@@H:12]([CH3:14])[CH2:11][C@H:10]1[C:15]1[NH:16][CH:17]=[C:18]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([C:30]2[CH:35]=[CH:34][C:33]([C:36]4[N:37]=[C:38]([C@@H:41]5[CH2:45][C@H:44]([CH3:46])[CH2:43][N:42]5C(OC(C)(C)C)=O)[NH:39][CH:40]=4)=[CH:32][CH:31]=2)[CH:24]=[CH:23]3)[N:19]=1)=O)(C)(C)C>O1CCOCC1.CO>[CH3:46][C@@H:44]1[CH2:43][NH:42][C@H:41]([C:38]2[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:10]7[CH2:11][C@H:12]([CH3:14])[CH2:13][NH:9]7)[NH:16][CH:17]=6)[CH:21]=5)[CH:26]=4)=[CH:31][CH:32]=3)[N:37]=2)[CH2:45]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178461445HCID 178461445, compound

Product 1

HCID 178461568HCID 178461568, 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(2S,4S)-2-(4-(4-(6-(2-((2S,4S)-1-(tert-butoxycarbonyl)-4-methyl-2-pyrrolidinyl)-1H-imidazol-4-yl)-2-naphthyl)phenyl)-1H-imidazol-2-yl)-4-methyl-1-pyrrolidinecarboxylate (200 mg. 0.285 mmol) in MeOH (5 mL) and stirred at ambient conditions for 2 hours, concentrated, and dried under vacuum. Tetra HCl salt (assume theoretical: 185 mg). LC-MS retention time 2.64 min; Calcd. for C32H35N6: 503.29 m/z Found 503.20 [M+H]+. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 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® Luna 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-b7185c1f4e8e422fab0646d47a6c6de0
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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