1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)carbamoyl)pyrrolidine-1-carboxylate

HRID 929307Notes

Reaction equation

HRID 929307 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:8]([NH:9][CH2:10][CH3:11])=[CH:7][N:6]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:5]=1.CCN(C(C)C)C(C)C.[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH:36]([C:39]([OH:41])=O)[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:3][C:4]1[C:8]([N:9]([CH2:10][CH3:11])[C:39]([CH:36]2[CH2:37][CH2:38][N:34]([C:32]([O:31][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:33])[CH2:35]2)=[O:41])=[CH:7][N:6]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:5]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 86705836HCID 86705836, compound

Product 1

HCID 90359912tert-butyl 3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)carbamoyl)pyrrolidine-1-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine dihydrochloride (0.20 g, 0.68 mmol) in CH2Cl2 (1.4 mL) were added DIPEA (0.35 g, 2.7 mmol) followed by 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (0.22 g, 1.0 mmol) and EDCI (0.20 g, 1.0 mmol). The reaction mixture was stirred at room temperature for 16 hours, then concentrated. The residue was purified by silica gel chromatography eluting with 0%-50% acetone/hexanes to afford a colorless oil (0.14 g, 49%).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with 0%-50% acetone/hexanes

Sources & evidence

ORD record
ord-01212b831ea44f3792aa690c587637a2
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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