Hydrochloric Acid → (3R)-N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochloride

HRID 72144Notes

Reaction equation

HRID 72144 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C@@H:10]2[CH2:14][CH2:13][N:12]([C:15]([NH:17][CH:18]3[CH2:24][CH:23]4[N:25](C(OC(C)(C)C)=O)[CH:20]([CH2:21][CH2:22]4)[CH2:19]3)=[O:16])[CH2:11]2)=[N:7][CH:8]=1)#[N:2].[ClH:33].O1CCOCC1>C(Cl)Cl>[ClH:33].[ClH:33].[CH:20]12[NH:25][CH:23]([CH2:22][CH2:21]1)[CH2:24][CH:18]([NH:17][C:15]([N:12]1[CH2:13][CH2:14][C@@H:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH2:11]1)=[O:16])[CH2:19]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66882921tert-butyl 3-((R)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 66884619(3R)-N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 3-((R)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxylate (49 mg, 0.11 mmol) was dissolved in CH2Cl2 (2.5 mL) and 4 M HCl in dioxane (0.8 mL, 3.2 mmol) was added. The mixture was stirred at rt for 1 h and concentrated to give (3R)—N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochloride (46 mg, quant).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-0fe736b121c54db6b06e7c7db3e656c7
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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