Phenylacetyl chloride → HCID 178520252, compound

HRID 82708Notes

Reaction equation

HRID 82708 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=3)C(=O)[O:9][N:8]=2)=[N:4][O:5][N:6]=1.[C:20]1([CH2:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:7](=[N:8][OH:9])[C:3]2[C:2]([NH:1][C:27](=[O:28])[CH2:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:6][O:5][N:4]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 585582673-(4-amino-1,2,5-oxadiazol-3-yl)-4-(3-chlorophenyl)-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 178520252HCID 178520252, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 3-(4-amino-1,2,5-oxadiazol-3-yl)-4-(3-chlorophenyl)-1,2,4-oxadiazol-5(4H)-one (30.0 mg, 0.107 mmol) and 4-dimethylaminopyridine (2.6 mg, 0.021 mmol) in pyridine (0.50 mL) was treated with benzeneacetyl chloride (42.6 μL, 0.322 mmol) and stirred for 4 h. The reaction mixture was concentrated and rediluted with ethanol (1.0 mL) and 2 M of sodium hydroxide in water (0.30 mL) stirred for 45 min. Purification of the crude reaction mixture by preparative HPLC gave the desired product (18 mg, 45%). LCMS for C17H15ClN5O3 (M+H)+: m/z=371.9.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionrediluted with ethanol (1.0 mL) and 2 M of sodium hydroxide in water (0.30 mL)
  3. stirringstirred for 45 min
  4. customPurification of the crude
  5. customreaction mixture by preparative HPLC

Sources & evidence

ORD record
ord-765ff6febd8d4b95a6066d9365b6054d
Source dataset
uspto-grants-2014_09
Patent number
US08846726B2

Reaction notes

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