Water → HCID 58997600, compound

HRID 1592063Notes

Reaction equation

HRID 1592063 reaction equation
[C:1]([C:3]1[C:4]([CH2:21][CH2:22][CH3:23])=[CH:5][C:6](OS(C(F)(F)F)(=O)=O)=[N:7][C:8]=1[S:9][CH2:10][C:11]#[N:12])#[N:2].[OH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)CC)C.O>O1CCOCC1>[NH2:2][C:1]1[C:3]2[C:8](=[N:7][C:6]([N:28]3[CH2:29][CH2:30][CH:25]([OH:24])[CH2:26][CH2:27]3)=[CH:5][C:4]=2[CH2:21][CH2:22][CH3:23])[S:9][C:10]=1[C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 58997595HCID 58997595, compound

Product 1

HCID 58997600HCID 58997600, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Trifluoro-methanesulfonic acid 5-cyano-6-cyanomethylsulfanyl-4-propyl-pyridin-2-yl ester (1.10 g, 3.00 mmol) (see Example 1, Method B) and 4-hydroxypiperidine (310 mg, 3.00 mmol) was suspended in 2 mL of dioxane. Triethylamine (0.84 mL, 6.0 mmol) was added and the reaction mixture was heated in a SmithSynthesizer™ (Personal Chemistry) at 100° C. for 2 h. This reaction mixture was poured into water and the resulting solid was collected by filtration and air dried to provide 3-amino-6-(4-hydroxy-piperidin-1-yl)-4-propyl-thieno[2,3-b]pyridine-2-carbonitrile (845 mg, 89%).

Workup

  1. filtrationthe resulting solid was collected by filtration and air
  2. customdried

Sources & evidence

ORD record
ord-70213d01d325424b84978b5599198386
Source dataset
uspto-grants-2007_11
Patent number
US07291733B2

Reaction notes

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