1,4-Dioxane hydrochloride → HCID 135550604, compound

HRID 1611160Notes

Reaction equation

HRID 1611160 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)[CH:5]=[C:4]([C:23]2[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:24]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:3]=1.[ClH:38].O1CCOCC1>O1CCOCC1>[ClH:38].[NH2:1][C:2]1[N:3]=[C:4]([C:23]2[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:24]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)[C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 135550623HCID 135550623, compound

Product 1

HCID 135550604HCID 135550604, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 3-{2-amino-6-[2-(benzyloxy)-6-hydroxyphenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate (239 mg, 0.48 mmol) in dioxane (25 mL) was added 4N HCl/dioxane (25 mL). The reaction mixture was stirred at room temperature overnight. The resulting precipitate was collected by filtration, washed with ethyl acetate and hexane, dried under reduced pressure to give 2-amino-6-[2-(benzyloxy)-6-hydroxyphenyl]-4-(3-piperidinyl)nicotinonitrile hydrochloride (184 mg, yield; 88%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with ethyl acetate and hexane
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-6925cce2994c45f69151152fd52f889d
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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