Pyridine → tert-butyl 3-(3-(4-chloro-2-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-ylcarbamoyl)phenylcarbamoyl)benzylthio)propanoate

HRID 926867Notes

Reaction equation

HRID 926867 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:8]=1)=[O:5].N1C=CC=CC=1.Cl[C:34]([C:36]1[CH:37]=[C:38]([CH:50]=[CH:51][CH:52]=1)[CH2:39][S:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:35]>ClCCl>[Cl:26][C:23]1[CH:24]=[CH:25][C:2]([NH:1][C:34]([C:36]2[CH:37]=[C:38]([CH:50]=[CH:51][CH:52]=2)[CH2:39][S:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:47])[CH3:48])=[O:44])=[O:35])=[C:3]([C:4](=[O:5])[NH:6][C:7]2[CH:11]=[CH:10][N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=3)[N:8]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 665876402-amino-5-chloro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamideHCID 86705208Tert-butyl 3-(3-(chlorocarbonyl)benzylthio)propanoate

Product 1

HCID 68069786tert-butyl 3-(3-(4-chloro-2-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-ylcarbamoyl)phenylcarbamoyl)benzylthio)propanoateYield 30.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round bottom flask, was placed a solution of 2-amino-5-chloro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzamide (191 mg, 0.50 mmol, 1.00 equiv) in dichloromethane (5 mL), pyridine (120 mg, 1.50 mmol, 3.00 equiv), and tert-butyl 3-(3-(chlorocarbonyl)benzylthio)propanoate (158 mg, 0.50 mmol, 1.00 equiv). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with 2×50 mL of water. The mixture was dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (20:1) to give 100 mg (30%) of product as yellow oil.

Workup

  1. customInto a 50-mL round bottom flask, was placed
  2. washThe resulting mixture was washed with 2×50 mL of water
  3. dry with materialThe mixture was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. washeluted with petroleum ether/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-7a97a2d2a8fd458e8bf733c00b8855a5
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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