3-Chloro-2-fluorobenzoic acid → HCID 66890990, compound

HRID 1897944Notes

Reaction equation

HRID 1897944 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:5]=[C:4]([NH:15][C:16]2[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:17]=2)[CH:3]=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.C(N(CC)CC)C>[Cl:29][C:30]1[C:31]([F:39])=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([N:12]1[CH2:11][CH2:10][CH:9]([CH2:8][C:6]2[N:5]=[C:4]([NH:15][C:16]3[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[N:17]=3)[CH:3]=[C:2]([CH3:1])[N:7]=2)[CH2:14][CH2:13]1)=[O:34]

Participants

8

Reactant 5

HCID 3029313-Chloro-2-fluorobenzoic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66889473HCID 66889473, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 66890990HCID 66890990, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 29.8 mg of 6-methyl-2-(piperidin-4-ylmethyl)-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyrimidin-4-amine in 2 ml of chloroform were added 39.1 mg of 3-chloro-2-fluorobenzoic acid, 0.093 ml of triethylamine, 29.5 mg of hydroxybenzotriazole hydrate and 43.8 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at room temperature, followed by stirring the reaction mixture at room temperature for 1.5 hours. 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=1/1 to ethyl acetate) to give the title compound.

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=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-8895e127ee704675ad132f628d76dc1c
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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