Propionyl chloride → HCID 66745328, compound

HRID 1959465Notes

Reaction equation

HRID 1959465 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[C:15]([NH2:26])=[N:16][CH:17]=[C:18]([C:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=4)[N:19]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:39])[CH2:37][CH3:38]>C(Cl)Cl>[NH2:26][C:15]1[N:16]=[CH:17][C:18]([C:20]2[CH2:21][CH2:22][N:23]([C:36](=[O:39])[CH2:37][CH3:38])[CH2:24][CH:25]=2)=[N:19][C:14]=1[C:12]1[O:13][C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][Br:1])=[CH:8][CH:7]=2)=[N:10][N:11]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 66745897HCID 66745897, compound

Product 1

HCID 66745328HCID 66745328, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine (34 mg, 0.07 mmol) in anhydrous DCM (500 μL) cooled in an ice water bath under an atmosphere of nitrogen was added DIEA (49 mg, 66 μL, 0.38 mmol) followed by the dropwise addition of a solution of propanoyl chloride (8 mg, 7 μL, 0.08 mmol) in DCM (0.2 mL). The reaction mixture was stirred for 15 minutes. The reaction mixture was diluted with DCM and washed three times with 1M aqueous HCl solution, twice with saturated aqueous NaHCO3 solution and then twice with a solution of brine. The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to yield 1-[4-[5-amino-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3,6-dihydro-2H-pyridin-1-yl]propan-1-one (20 mg, 57%). LC/MS m/z 471.3 [M+H]+.

Workup

  1. washwashed three times with 1M aqueous HCl solution
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b7ae991e6152459f9b18c3dfbf6923e4
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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