3-Chloro-2-fluorobenzoic acid → HCID 58097106, compound

HRID 1897950Notes

Reaction equation

HRID 1897950 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:29][C:30]1[C:31]([F:39])=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](O)=[O:34].O.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22][N:21]([C:33](=[O:34])[C:32]4[CH:36]=[CH:37][CH:38]=[C:30]([Cl:29])[C:31]=4[F:39])[CH2:20][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 3029313-Chloro-2-fluorobenzoic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58097129HCID 58097129, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 58097106HCID 58097106, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 230 mg of ethyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-4-carboxylate in 10 ml of chloroform were added 156 mg of 3-chloro-2-fluorobenzoic acid, 137 mg of hydroxybenzotriazole hydrate and 229 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at room temperature, followed by stirring the reaction mixture at room temperature overnight. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The resulting ethyl acetate layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1) to give the title compound as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe resulting ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-f1ff85bd030b41a6b8ba215f9b231afa
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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