Pyridine → Methyl 3-(3-((4-(piperidin-1-yl)-2-((2-(3-(trifluoromethyl)phenyl)pyrimidin-5-yl)carbamoyl)phenyl)carbamoyl)-benzylthio)propanoate

HRID 926767Notes

Reaction equation

HRID 926767 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[N:11][CH:12]=1)=[O:5].Cl[C:34]([C:36]1[CH:37]=[C:38]([CH:47]=[CH:48][CH:49]=1)[CH2:39][S:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])=[O:35].N1C=CC=CC=1>O1CCCC1.O>[N:27]1([C:24]2[CH:25]=[CH:26][C:2]([NH:1][C:34]([C:36]3[CH:37]=[C:38]([CH:47]=[CH:48][CH:49]=3)[CH2:39][S:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])=[O:35])=[C:3]([C:4](=[O:5])[NH:6][C:7]3[CH:8]=[N:9][C:10]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=4)=[N:11][CH:12]=3)[CH:23]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 665877992-amino-5-(piperidin-1-yl)-N-(2-(3-(trifluoromethyl)phenyl)pyrimidin-5-yl)benzamideHCID 86705202Methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate

Product 1

HCID 66586920Methyl 3-(3-((4-(piperidin-1-yl)-2-((2-(3-(trifluoromethyl)phenyl)pyrimidin-5-yl)carbamoyl)phenyl)carbamoyl)-benzylthio)propanoateYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 50-mL 3-necked round-bottom flask, was placed 2-amino-5-(piperidin-1-yl)-N-(2-(3-(trifluoromethyl)phenyl)pyrimidin-5-yl)benzamide (234 mg, 0.53 mmol, 1.00 equiv), tetrahydrofuran (5 mL), a solution of methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate (145 mg, 0.53 mmol, 1.00 equiv) in tetrahydrofuran (5 mL), and pyridine (80 mg, 1.01 mmol, 2.00 equiv). The resulting solution was stirred for 4 h at room temperature. The reaction was diluted with 10 mL of water and then extracted with 2×20 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under vacuum to afford 0.28 g (78%) of product as a yellow solid.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask, was placed
  2. extractionextracted with 2×20 mL of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ddf0815f4a4b4e269a0bf0ea47e406f8
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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