Water → HCID 58997601, compound

HRID 1592066Notes

Reaction equation

HRID 1592066 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].[O:24]1[C:28]2([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[O:27][CH2:26][CH2:25]1.C(N(CC)CC)C.O>O1CCOCC1>[NH2:2][C:1]1[C:3]2[C:8](=[N:7][C:6]([N:31]3[CH2:32][CH2:33][C:28]4([O:27][CH2:26][CH2:25][O:24]4)[CH2:29][CH2:30]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 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 58997595HCID 58997595, compound

Product 1

HCID 58997601HCID 58997601, compoundYield 88%

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 (1.83 g, 5.00 mmol) (see Example 1, Method B) and 1,4-dioxa-8-aza-spiro[4.5]decane (0.66 mL, 5.00 mmol) were suspended in 3 mL of dioxane. Triethylamine (0.84 mL, 6.0 mmol) was added. The reaction mixture was heated in a SmithSynthesizer™ (Personal Chemistry) at 100° C. for 2 h. The reaction mixture was poured into water and the resulting solid was collected by filtration and recrystallized from acetonitrile to give 3-amino-6-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-propyl-thieno[2,3-b]pyridine-2-carbonitrile as a yellow solid (1.57 g, 88%).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-4e77acbdbc5e44fa8bbf740e7083cbd2
Source dataset
uspto-grants-2007_11
Patent number
US07291733B2

Reaction notes

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