3-Chloro-2-fluorobenzoic acid → 5-(4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-1-(3-chloro-2-fluorobenzoyl)piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 1897961Notes

Reaction equation

HRID 1897961 reaction equation
Cl.Cl.[C:3]([N:7]1[C:11]([NH:12][C:13]2[N:18]=[C:17]([CH2:19][C:20]3([C:26]4[O:30][C:29](=[O:31])[NH:28][N:27]=4)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[N:8]1)([CH3:6])([CH3:5])[CH3:4].[Cl:32][C:33]1[C:34]([F:42])=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](O)=[O:37].Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1>[C:3]([N:7]1[C:11]([NH:12][C:13]2[N:18]=[C:17]([CH2:19][C:20]3([C:26]4[O:30][C:29](=[O:31])[NH:28][N:27]=4)[CH2:21][CH2:22][N:23]([C:36](=[O:37])[C:35]4[CH:39]=[CH:40][CH:41]=[C:33]([Cl:32])[C:34]=4[F:42])[CH2:24][CH2:25]3)[CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[N:8]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 3029313-Chloro-2-fluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66890171HCID 66890171, compound

Product 1

HCID 580971095-(4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-1-(3-chloro-2-fluorobenzoyl)piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 40 mg of 5-(4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one dihydrochloride in 2 ml of pyridine were added 17.8 mg of 3-chloro-2-fluorobenzoic acid and 24.4 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at room temperature. The reaction mixture was stirred at room temperature overnight, followed by concentrating in vacuo. The reaction mixture was dissolved in ethyl acetate, and washed with water. 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: hexane to ethyl acetate) to give the title compound as a pale yellow oil.

Workup

  1. concentrationby concentrating in vacuo
  2. dissolutionThe reaction mixture was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe resulting ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane to ethyl acetate)

Sources & evidence

ORD record
ord-12d4f2d351c44a12a54d0fe4af6637df
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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