3-Chloro-2-fluorobenzoic acid → 1-(3-chloro-2-fluorobenzoyl)-4-((6-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyridin-2-yl)methyl)piperidin-4-ol

HRID 1897939Notes

Reaction equation

HRID 1897939 reaction equation
[CH3:1][Si:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([CH2:19][C:20]3([OH:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:16]=[CH:15][CH:14]=2)=[N:8]1.[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>[Cl:29][C:30]1[C:31]([F:39])=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([N:23]1[CH2:22][CH2:21][C:20]([CH2:19][C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:12][C:9]3[CH:10]=[CH:11][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:27])([CH3:1])[CH3:28])[N:8]=3)[N:18]=2)([OH:26])[CH2:25][CH2:24]1)=[O:34]

Participants

7

Reactant 5

HCID 3029313-Chloro-2-fluorobenzoic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668894454-((6-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyridin-2-yl)methyl)piperidin-4-olHCID 178526939HCID 178526939, compound

Product 1

HCID 668907351-(3-chloro-2-fluorobenzoyl)-4-((6-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyridin-2-yl)methyl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 204 mg of 4-((6-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyridin-2-yl)methyl)piperidin-4-ol in 10 ml of chloroform were added 132 mg of 3-chloro-2-fluorobenzoic acid, 116 mg of hydroxybenzotriazole hydrate and 194 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 chloroform. The resulting chloroform 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: hexane/ethyl acetate=10/1 to ethyl acetate) to give the title compound as a colorless oil.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe resulting chloroform 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: hexane/ethyl acetate=10/1 to ethyl acetate)

Sources & evidence

ORD record
ord-f98acdb622814f75b5c7a52493692e89
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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