Triethylamine → N-(3-(2,4-Dichlorophenyl)-2,6-dimethylpyrazolo[5,1-b]oxazol-7-yl) propionamide

HRID 1671301Notes

Reaction equation

HRID 1671301 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([NH2:19])=[C:11]2[O:12][C:13]=1[CH3:14].C(N(CC)CC)C.[C:27](Cl)(=[O:30])[CH2:28][CH3:29]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([NH:19][C:27](=[O:30])[CH2:28][CH3:29])=[C:11]2[O:12][C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 59186059HCID 59186059, compound

Product 1

HCID 44815707N-(3-(2,4-Dichlorophenyl)-2,6-dimethylpyrazolo[5,1-b]oxazol-7-yl) propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-ylamine (Intermediate ID) (500 mg, 1.503 mmol) in DCM (10 ml) under N2 is added triethylamine (0.461 ml, 3.31 mmol) followed by propionyl chloride (0.144 ml, 1.654 mmol) at 0° C. After 2 hr, the reaction mixture is diluted with DCM (50 ml) and washed with 1M HCl, NaHCO3, Brine, dried (MgSO4) and evaporated down to give a pink solid. This is then triturated with Et2O to give the title compound as an off white solid. MS: n/z 351.9[M+H]+

Workup

  1. washwashed with 1M HCl, NaHCO3, Brine
  2. dry with materialdried (MgSO4)
  3. customevaporated down
  4. customto give a pink solid
  5. customThis is then triturated with Et2O

Sources & evidence

ORD record
ord-00fe4b6851a143d0ad06ef1c4f1c22a5
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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