Pyrrolidine → (4-((5-bromo-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone

HRID 1051442Notes

Reaction equation

HRID 1051442 reaction equation
[Br:1][C:2]1[N:6]([CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[N:5]=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Br:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:14])=[CH:15][CH:16]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 86583742Edc hobtHCID 867292264-((5-bromo-1H-pyrazol-1-yl)methyl)benzoic acid

Product 1

HCID 86729227(4-((5-bromo-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanoneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-((5-bromo-1H-pyrazol-1-yl)methyl)benzoic acid (200 mg, 0.71 mmol), pyrrolidine (61 mg, 0.85 mmol) and EDC-HOBt (452 mg, 2 mmol) were combined in CH2Cl2 and stirred for 4 h at room temperature. The mixture was evaporated in vacuuo and the residue dissolved in ethyl acetate and washed with water. The separated organic layer was dried and concentrated affording the product as an oil (231 mg, yield 99%), which was used in next step without further purification. LCMS (m/z): 334.2 [M+H]+

Workup

  1. customThe mixture was evaporated in vacuuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water
  4. customThe separated organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b1980fac96a4bf4b57e9eb2d1bc5de5
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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