Ammonium Chloride → HCID 178513486, compound

HRID 1897952Notes

Reaction equation

HRID 1897952 reaction equation
[Cl:1][C:2]1[C:3]([F:32])=[C:4]([CH:29]=[CH:30][CH:31]=1)[C:5]([N:7]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]3[CH:28]=[CH:27][NH:26][N:25]=3)[N:18]=2)([C:13]([OH:15])=O)[CH2:9][CH2:8]1)=[O:6].[Cl-].[NH4+].O.OC1C2N=N[NH:42]C=2C=CC=1.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([F:32])=[C:4]([CH:29]=[CH:30][CH:31]=1)[C:5]([N:7]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]3[CH:28]=[CH:27][NH:26][N:25]=3)[N:18]=2)([C:13]([NH2:42])=[O:15])[CH2:9][CH2:8]1)=[O:6]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178519569HCID 178519569, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 178513486HCID 178513486, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 82.8 mg of 1-(3-chloro-2-fluorobenzoyl)-4-((6-(1H-pyrazol-3-ylamino)pyridin-2-yl)methyl)piperidine-4-carboxylic acid in 5 ml of chloroform were added 97 mg of ammonium chloride, 0.252 ml of triethylamine, 83 mg of hydroxybenzotriazole hydrate and 104 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 preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=6/1) to give the title compound as a pale yellow solid.

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 preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=6/1)

Sources & evidence

ORD record
ord-3f22aaf9e782419f810554a4753061a8
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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