Hydrochloric Acid → 5-{3-[1-aminoethyl]-5-chloro-6-cyano-2-ethoxyphenyl}-N,N-dimethylpyridine-2-carboxamide

HRID 510980Notes

Reaction equation

HRID 510980 reaction equation
[Cl:1][C:2]1[C:3]([C:32]#[N:33])=[C:4]([C:21]2[CH:22]=[N:23][C:24]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[CH:25][CH:26]=2)[C:5]([O:18][CH2:19][CH3:20])=[C:6]([CH:8]([NH:10]C(=O)OC(C)(C)C)[CH3:9])[CH:7]=1.Cl>O1CCOCC1>[NH2:10][CH:8]([C:6]1[C:5]([O:18][CH2:19][CH3:20])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([N:29]([CH3:30])[CH3:31])=[O:28])=[N:23][CH:22]=2)[C:3]([C:32]#[N:33])=[C:2]([Cl:1])[CH:7]=1)[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 88540918Tert-butyl[1-(5-chloro-4-cyano-3-{6-[(dimethylamino)carbonyl]pyridin-3-yl}-2-ethoxyphenyl)ethyl]carbamate

Product 1

HCID 866668945-{3-[1-aminoethyl]-5-chloro-6-cyano-2-ethoxyphenyl}-N,N-dimethylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The tert-butyl [1-(5-chloro-4-cyano-3-{6-[(dimethylamino)carbonyl]pyridin-3-yl}-2-ethoxyphenyl)ethyl]carbamate from the above step (0.04 g, 0.085 mmol) was treated with 4 M HCl in dioxane (4 mL) and stirred at room temperature for 1 hour. The reaction was concentrated in vacuo to give 5-{3-[1-aminoethyl]-5-chloro-6-cyano-2-ethoxyphenyl}-N,N-dimethylpyridine-2-carboxamide as a semi-solid residue (0.05 g, 100%). LCMS calculated for C19H22ClN4O2 (M+H)+: m/z=373.1. found: 373.1.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-9cdb07bcef8343e8a956310c29b42be6
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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