Hydrochloric Acid → HCID 66982045, compound

HRID 625645Notes

Reaction equation

HRID 625645 reaction equation
[ClH:1].C(OC([N:9]1[C@@H:13]([CH3:14])[CH2:12][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)[N:32]=[C:31]([C:36]3[NH:40][C:39]([C@@H:41]5[CH2:45][CH2:44][C@H:43]([CH3:46])[N:42]5C(OC(C)(C)C)=O)=[N:38][CH:37]=3)[CH:30]=[CH:29]4)=[CH:22][CH:21]=2)=[CH:18][N:19]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[CH3:46][C@@H:43]1[NH:42][C@H:41]([C:39]2[NH:40][C:36]([C:31]3[CH:30]=[CH:29][C:28]4[C:33](=[CH:34][CH:35]=[C:26]([C:23]5[CH:22]=[CH:21][C:20]([C:17]6[NH:16][C:15]([C@@H:10]7[CH2:11][CH2:12][C@H:13]([CH3:14])[NH:9]7)=[N:19][CH:18]=6)=[CH:25][CH:24]=5)[CH:27]=4)[N:32]=3)=[CH:37][N:38]=2)[CH2:45][CH2:44]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66982311HCID 66982311, compound

Product 2

HCID 313Hydrochloric AcidHCID 66982045HCID 66982045, compoundYield 199.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M HCl (0.2 mL, 0.8 mmol) in dioxane was added to a solution of (2S,5S)-tert-butyl 2-(5-(6-(4-(2-((2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)quinolin-2-yl)-1H-imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate (12.7 mg, 0.018 mmol) in dioxane (1 mL) and the mixture was stirred at rt for 3 d. The reaction mixture was concentrated to yield a crude HCl salt of 2-(2-((2S,5S)-5-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)-6-(4-(2-((2S,5S)-5-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)quinoline (18.1 mg) as yellow solid. LC-MS retention time 2.597 min; m/z 504.46 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 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 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode. 1H NMR (400 MHz, MeOD) δ ppm 9.09 (d, J=9.0 Hz, 1H), 8.66 (s, 1H), 8.54-8.61 (m, 2H), 8.51 (d, J=9.0 Hz, 1H), 8.50 (d, J=8.8 Hz, 1H), 8.00-8.08 (m, 4H), 7.99 (s, 1H), 5.14 (t, J=8.5 Hz, 1H), 5.07 (t, J=8.0 Hz, 1H), 3.90-4.04 (m, 2H), 2.52-2.75 (m, 4H), 2.39-2.53 (m, 2H), 1.98-2.14 (m, 2H), 1.59 (dd, J=9.7, 6.7 Hz, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-2e1ac39939c345c19b69224af0870348
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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