Pyridine → Methyl 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzylthio)propanoate

HRID 625312Notes

Reaction equation

HRID 625312 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][NH:7][C:8](=[O:22])[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])[CH:10]=1.N1C=CC=CC=1.Cl[C:35]([C:37]1[CH:38]=[C:39]([CH:48]=[CH:49][CH:50]=1)[CH2:40][S:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])=[O:36]>O1CCCC1>[F:27][C:2]([F:26])([F:1])[C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][NH:7][C:8]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:35]([C:37]2[CH:38]=[C:39]([CH:48]=[CH:49][CH:50]=2)[CH2:40][S:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])=[O:36])[CH:10]=1)=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66588070N-(3-(trifluoromethyl)benzyl)-2-(2-aminophenyl)isonicotinamideHCID 86705202Methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate

Product 1

HCID 66586726Methyl 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzylthio)propanoateYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 100-mL round bottom flask, was placed a solution of N-(3-(trifluoromethyl)benzyl)-2-(2-aminophenyl)isonicotinamide (240 mg, 0.65 mmol, 1.00 equiv) in tetrahydrofuran (5 mL), and pyridine (77 mg, 0.97 mmol, 1.50 equiv). This was followed by dropwise addition of a solution of methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate (194 mg, 0.71 mmol, 1.10 equiv) in tetrahydrofuran (5 mL) with stirring. The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched with 30 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and dried over magnesium sulfate. The resulting mixture was concentrated under vacuum to yield 250 mg (64%) of product as a light yellow solid.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. stirringThe resulting solution was stirred for 2 h at room temperature
  3. customThe reaction was then quenched with 30 mL of water
  4. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-9f565607aed048efb55b3e50ac55f95b
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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