1-(2-Hydroxyethyl)piperazine → HCID 86687151, compound

HRID 2282595Notes

Reaction equation

HRID 2282595 reaction equation
Cl[C:2]1[N:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[OH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CC(N(C)C)=O>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([N:18]3[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][OH:12])[CH2:16][CH2:17]3)=[N:3][N:4]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 86687151HCID 86687151, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of Intermediate 24b (485 mg, 2.82 mmol) and 1-(2-hydroxylethyl)-piperazine (1.39 mL, 11.3 mmol) in DMA (10 mL) was heated in the microwave at 170° C. for 8 h. The cooled mixture was concentrated in vacuo. The residue was purified by FCC, using 0-20% (2M NH3 in MeOH) in DCM, to give impure product. Further purified by FCC, using 0-7% (2M NH3 in MeOH) in DCM gave the title compound as a pale brown gum (175 mg, 23%). LCMS (Method 3): Rt 0.43 min, m/z 266 [MH+].

Workup

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. customThe residue was purified by FCC
  3. customto give impure product
  4. customFurther purified by FCC

Sources & evidence

ORD record
ord-398c7b8f3cc14b23809f1ddda2217283
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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