1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-Fluoro-pyridine-2-carboxylic Acid (6-chloro-5-propyl-pyrimidin-4-ylmethyl)-(3-methyl-butyl)-amide

HRID 898704Notes

Reaction equation

HRID 898704 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][NH:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]=1[CH2:15][CH2:16][CH3:17].[F:18][C:19]1[N:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[CH:21][CH:20]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]([CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])[C:25]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([F:18])[N:24]=2)=[O:26])[C:3]=1[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2260276-Fluoropyridine-2-carboxylic acidHCID 58661552(6-Chloro-5-propyl-pyrimidin-4-ylmethyl)-(3-methyl-butyl)-amine

Product 1

HCID 586615506-Fluoro-pyridine-2-carboxylic Acid (6-chloro-5-propyl-pyrimidin-4-ylmethyl)-(3-methyl-butyl)-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (6-chloro-5-propyl-pyrimidin-4-ylmethyl)-(3-methyl-butyl)-amine (0.715 g, 2.8 mmol) and 6-fluoro-pyridine-2-carboxylic acid (0.47 g, 3.34 mmol) in DCM (10 ml) is added EDCI (0.61 g) and DMAP (0.153 g). The mixture is stirred at room temperature overnight. DCM (10 ml) is added to dilute the mixture. The mixture is washed with water (5 mL), dried (Na2SO4) and solvent evaporated. Preparative TLC purification of the residue (2:1 of hexane: ethyl acetate) provides the title product. H1 NMR δ (CDCl3) 8.69 and 8.75 (s, 1H), 7.71-7.97 (m,1H), 7.58-60 (m, 1H), 4.79 and 5.07 (s, 2H), 3.50-3.64 (m, 21), 2.59-2.87 (m, 2H), 1.45-1.72 (m,5H), 0.92-1.09 (m, 4H), 0.81 (d, 6H).

Workup

  1. additionto dilute the mixture
  2. washThe mixture is washed with water (5 mL)
  3. dry with materialdried (Na2SO4) and solvent
  4. customevaporated
  5. customPreparative TLC purification of the residue (2:1 of hexane: ethyl acetate)

Sources & evidence

ORD record
ord-1ac2e11b2a514b949b5fa48b073e2a7d
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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