Hydrochloric Acid → HCID 86690347, compound

HRID 2409897Notes

Reaction equation

HRID 2409897 reaction equation
[ClH:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][C@@H:14]3[CH2:16][C@H:11]2[C@@H:12]([NH:17][C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[NH:24]C(=O)OC(C)(C)C)[CH2:13]3)=[CH:6][CH:5]=1)#[N:3].CO>O1CCOCC1>[ClH:1].[ClH:1].[NH2:24][C@@H:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C@H:18]1[NH:17][C@@H:12]1[C@H:11]2[CH2:16][C@H:14]([CH2:15][N:10]2[C:7]2[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[CH:5][CH:6]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86690348HCID 86690348, compound

Product 1

HCID 86690347HCID 86690347, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl (4.0 N in 1,4-dioxane, 2 ml)) was added to a mixture of tert-butyl (1R,2R)-2-((1S,4S,6S)-2-(4-cyanophenyl)-2-azabicyclo[2.2.1]heptan-6-ylamino)cyclohexylcarbamate (445 mg, 1.084 mmol) in 1,4-dioxane (2 ml). The starting material formed a gum. MeOH (1 mL) was then added. Eventually all solids went into solution. The reaction was stirred at rt for 2 hrs. The reaction mixture was concentrated to give 4-((1R,4R,6S)-6-((1R,2R)-2-aminocyclohexylamino)-2-azabicyclo[2.2.1]heptan-2-yl)benzonitrile bishydrochloride (440 mg, 1.084 mmol, 100% yield) of an off white solid. Calcd. for C19H26N4 m/z 310.4, found: 311.2 (M+H)+.

Workup

  1. customThe starting material formed a gum
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-eeb24a43ac434447b130ef9660353048
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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