Ethylene Glycol → HCID 86640819, compound

HRID 2070910Notes

Reaction equation

HRID 2070910 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.N[C:19]1[N:35]=[C:22]2[CH:23]=CC=[C:26]([C:27]([CH:29]3[CH2:34][CH2:33]OCC3)=O)[N:21]2N=1.O.NN.[OH-].[K+].Cl.C(O)[CH2:43][OH:44]>O>[CH3:43][O:44][CH2:23][C:22]1[NH:21][C:26]2[CH:27]=[C:29]([C:9]3[CH:10]=[CH:11][C:12]4[N:13]([N:14]=[C:15]([NH2:17])[N:16]=4)[C:8]=3[CH2:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:34]=[CH:33][C:19]=2[N:35]=1

Participants

8

Reactant 6

HCID 174Ethylene Glycol2×HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 68587259HCID 68587259, compoundHCID 68588725HCID 68588725, compound

Product 1

HCID 86640819HCID 86640819, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

5-((Tetrahydro-2H-pyran-4-yl)methyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine. To a solution of (2-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone (8 g, 32.5 mmol) in ethylene glycol (100 mL) was added hydrazine monohydrate (8.16 mL, 260 mmol) and the reaction mixture was stirred for 5 min until a clear solution was obtained. Solid potassium hydroxide (3.65 g, 65.0 mmol) dissolved in ethylene glycol (20 mL) was added and the reaction mixture was heated at 160° C. for 16 h. Water (100 mL) was added to the reaction, and it was neutralized to pH=7 with hydrochloric acid. The reaction was then extracted with ethyl acetate (2×400 mL). The combined organics were dried over magnesium sulfate, filtered, concentrated on a rotary evaporator to give the desired product (7 g, 30.1 mmol, 93% yield) as an off white solid. MS (ESI) m/z 233.2 [M+1]+. This material was used without further purification in the next step.

Workup

  1. customwas obtained
  2. additionwas added
  3. extractionThe reaction was then extracted with ethyl acetate (2×400 mL)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-754d5aeb672d42e1894242a57f91264a
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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