1,2-Dichloroethane → HCID 178449063, compound

HRID 528925Notes

Reaction equation

HRID 528925 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[N:2]1.C(Cl)CCl.C1[CH:14]=[CH:15][C:16]2N(O)N=[N:19][C:17]=2C=1.C(N(C(C)C)C(C)C)C.[CH2:32](N)[CH2:33][CH2:34][CH3:35]>CN(C=O)C>[CH2:32]([N:19]([CH2:17][CH2:16][CH2:15][CH3:14])[C:6]([C:3]1[CH:4]=[CH:5][NH:1][N:2]=1)=[O:8])[CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8007ButylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178524567HCID 178524567, compound

Product 1

HCID 178449063HCID 178449063, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1H-pyrazole-3-carboxylic acid (Matrix, 350 mg, 3.12 mmol) in DMF (8.7 mL) were added EDC (658 mg, 3.43 mmol), HOBT (622 mg, 4.06 mmol), i-Pr2EtN (1.6 mL, 9.37 mmol) and n-butylamine (550 μL, 3.28 mmol). The resulting solution was stirred at room temperature overnight. The reaction mixture was then quenched with sat. aq. NH4Cl solution, washed with 1N aq. HCl solution and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified using flash column chromatography (gradient from 0% to 5% (MeOH/CH2Cl2) to give the title compound (530 mg, 76%) as a colorless crystalline solid. 1H NMR (CD3OD, 1.5:1 mixture of amide rotamers) δ 7.74 (br s, 1H), 6.67 (br s, 1H), 6.38 (br s, 1H), 3.70-3.39 (m, 4H), 1.64 (quin, J=7.6 Hz, 4H), 1.36 (dt, J=14.4, 7.0 Hz, 4H), 1.04-0.88 (m, 6H); MS(ESI+) m/z 224.3 (M+H)+.

Workup

  1. customThe reaction mixture was then quenched with sat. aq. NH4Cl solution
  2. washwashed with 1N aq. HCl solution
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude oil was purified

Sources & evidence

ORD record
ord-b9e4871b0d334bc58949f27fbc346ea1
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

Loading…