Hydrochloric Acid → HCID 86279105, compound

HRID 588390Notes

Reaction equation

HRID 588390 reaction equation
[Cl:1][C:2]1[C:3]([N:8]([C@@H:28]2[CH2:33][CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]2)[C:9](=[O:27])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[N:18][N:19]([CH3:26])[C:20]=3[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl>C(Cl)Cl>[Cl:1][C:2]1[C:3]([N:8]([C@@H:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)[C:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[N:18][N:19]([CH3:26])[C:20]=3[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][CH:11]=2)=[O:27])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117652912HCID 117652912, compound

Product 1

HCID 86279105HCID 86279105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound from Preparation 18 (R)-tert-Butyl 3-(N-(3-chloropyridin-2-yl)-4-(5-(ethoxycarbonyl)-1-methyl-1H-pyrazol-4-yl)benzamido)piperidine-1-carboxylate (145.87 g, 256.8 mmol) was dissolved in 1.4 L of DCM and then treated with hydrochloric acid (3 mol/L in cyclopentyl methyl ether, 428 mL, 1284 mmol). The reaction was stirred at room temperature for 19 h then 500 mL of DCM was added followed by warming to 40° C. and then filtering through Celite®. The filtrate was concentrated to 500 mL total volume in vacuo and then added to 1.4 L of EtOAc, resulting in precipitation of solids which were isolated via filtration. After drying, the hydrochloride salt of the title compound was isolated as an off-white solid (125.2 g, 97%).

Workup

  1. temperatureby warming to 40° C.
  2. filtrationfiltering through Celite®
  3. concentrationThe filtrate was concentrated to 500 mL total volume in vacuo
  4. additionadded to 1.4 L of EtOAc
  5. customresulting in precipitation of solids which
  6. customwere isolated via filtration
  7. customAfter drying

Sources & evidence

ORD record
ord-790ebb201bdb498b8c0ac08f0544648e
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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