Hydrochloric Acid → N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-(1-piperidinyl)propanamide hydrochloride

HRID 2218252Notes

Reaction equation

HRID 2218252 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:26])[CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][Si](C(C)(C)C)(C)C)[N:3]=1.[ClH:41]>O1CCOCC1>[ClH:41].[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:26])[CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69144979N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-3-(1-piperidinyl)propanamide

Product 1

HCID 135456002N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-(1-piperidinyl)propanamide hydrochlorideYield 9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]-phenyl}-3-(1-piperidinyl)propanamide (0.150 g, 0.270 mmol) in 1,4-dioxane (5 mL) was added 4N HCl in dioxane (2 mL). The mixture was stirred at room temperature for 12 hrs. The resulting precipitate was collected by filtration, washed with ethanol, and dried under reduced pressure to give N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-(1-piperidinyl)propanamide hydrochloride (0.011 g, yield 9%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with ethanol
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-5c26f4b2791e44c0b4c872e25c1b3a77
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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