Water → N-(4-tert-Butylphenyl)-1-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 1246696Notes

Reaction equation

HRID 1246696 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH:12]=[C:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].CCN=C=NCCCN(C)C.O>ClCCl>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([NH:25][C:14]([C:11]2[CH2:10][CH2:9][N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:13][CH:12]=2)=[O:16])=[CH:26][CH:27]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 698614-Tert-ButylanilineHCID 219047271-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid

Product 1

HCID 11474160N-(4-tert-Butylphenyl)-1-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3′-Chloro-3,6-dihydro-2H-1,2′-bipyridine-4-carboxylic acid (120 mg, 0.35 mmol), 4-tert-butylaniline (90.0 mg, 0.6 mmol), and EDCI (145 mg, 0.75 mmol) were combined in dichloromethane (3 mL) under N2 and stirred at room temperature overnight. The mixture was treated with water and the layers were separated. The organic layer was concentrated and the residue was purified via column chromatography (SiO2, ethyl acetate:hexanes, 1:4) to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 8.18 (dd, 1H), 7.61 (dd, 1H), 7.46 (d, 2H), 7.38 (s(br), 1H), 7.35 (d, 2H), 6.85 (dd, 1H), 6.75 (m, 1H), 4.10 (dd, 2H), 3.58 (dd, 2H), 2.68 (m, 2H), 1.30 (s, 9H); MS (ESI) 370 (M+H)+.

Workup

  1. customthe layers were separated
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified via column chromatography (SiO2, ethyl acetate:hexanes, 1:4)

Sources & evidence

ORD record
ord-4f0624d31cf24b35994bb5c1fcfa5771
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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