Hydrochloric Acid → Hydrochloric Acid

HRID 1752293Notes

Reaction equation

HRID 1752293 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]([C@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3C(OC(C)(C)C)=O)[S:10][CH:11]=2)=[CH:3][CH:2]=1.[ClH:24]>C(Cl)Cl.O1CCOCC1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:8]=[C:9]([C@H:12]3[CH2:16][CH2:15][CH2:14][NH:13]3)[S:10][CH:11]=2)=[CH:5][CH:6]=1.[ClH:24]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67480237(R)-tert-butyl 2-(4-(pyridin-4-yl)thiazol-2-yl)pyrrolidine-1-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 58171617(R)-4-(pyridin-4-yl)-2-(pyrrolidin-2-yl)thiazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A 31-mg aliquot of crude product from Step 2 was dissolved in CH2Cl2 (3 mL) and 4 M HCl in dioxane (1 mL) was added. The mixture was stirred at rt for 2 h and concentrated to leave (R)-4-(pyridin-4-yl)-2-(pyrrolidin-2-yl)thiazole as its HCl salt (35 mg). LC-MS Method 1 tR=0.40 min, m/z=232.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-c42f5eb024ff432b8e31c3771f9d3ce2
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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