Hydrochloric Acid → HCID 178461572, compound

HRID 625654Notes

Reaction equation

HRID 625654 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][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:27]=[C:28]4[C:33](=[CH:34][CH:35]=3)[CH:32]=[C:31]([C:36]3[NH:40][C:39]([C@@H:41]5[CH2:45][C@H:44]([CH3:46])[CH2:43][N:42]5C(OC(C)(C)C)=O)=[N:38][C:37]=3[Cl:54])[CH:30]=[CH:29]4)=[CH:22][CH:21]=2)=[CH:18][N:19]=1)=O)(C)(C)C>O1CCOCC1.CO>[Cl:54][C:37]1[N:38]=[C:39]([C@@H:41]2[CH2:45][C@H:44]([CH3:46])[CH2:43][NH:42]2)[NH:40][C:36]=1[C:31]1[CH:30]=[CH:29][C:28]2[C:33](=[CH:34][CH:35]=[C:26]([C:23]3[CH:22]=[CH:21][C:20]([C:17]4[NH:16][C:15]([C@@H:10]5[CH2:11][C@H:12]([CH3:14])[CH2:13][NH:9]5)=[N:19][CH:18]=4)=[CH:25][CH:24]=3)[CH:27]=2)[CH:32]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178461456HCID 178461456, compound

Product 1

HCID 178461572HCID 178461572, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4N HCl in dioxane (5 mL) was added to a stirred solution of (2S,4S)-tert-butyl 2-(5-(6-(4-(2-((2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-4-chloro-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate (30 mg, 0.041 mmol) in MeOH (1 mL) and the mixture was stirred at RT for 2 h, concentrated, and dried under high vacuum for 2 h. LC-MS retention time 3.31 min; calcd. for C32H34ClN6: 537 26 m/z Found 537.37 [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 high vacuum for 2 h
  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-2d117ed3279e48069fb5c428839fbb05
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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