Pyridinium.p-toluenesulfonate → HCID 86640470, compound

HRID 1807111Notes

Reaction equation

HRID 1807111 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[C:19]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)([C:28]#[N:29])[CH:18]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[NH:17]3)=[O:15])=[N:9]2)[CH2:4][O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]2[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:19]([C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)([C:28]#[N:29])[CH:18]([CH2:37][C:38]([CH3:39])([CH3:40])[CH3:41])[NH:17]2)=[O:15])=[N:9]1

Participants

4

Reactant 2

HCID 22033616Pyridinium.p-toluenesulfonateHCID 86640469HCID 86640469, compound

Product 1

HCID 86640470HCID 86640470, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-amide (81 mg, 0.133 mmol), pyridinium p-toluene sulfonic acid (5 mg, 0.0198 mmol) and methanol (4 mL) was microwaved at 120° C. for 5 min. Solvent evaporated and purified by reverse phase chromatography (20-95% of ACN/water) to rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide (26.5 mg, 35%) as an off-white powder. HRMS (ES+) m/z Calcd for C29H33Cl2N5O3S+H [(M+H)+]: 570.2033. found: 570.2032.

Workup

  1. customwas microwaved at 120° C. for 5 min
  2. customSolvent evaporated
  3. custompurified by reverse phase chromatography (20-95% of ACN/water) to rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide (26.5 mg, 35%) as an off-white powder

Sources & evidence

ORD record
ord-c0d41e446c9b498ca21c2ca5a0cf24d8
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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