Pyridine → tert-butyl 3-(3-(4-chloro-2-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl-carbamoyl)phenylcarbamoyl)benzylthio)propanoate

HRID 926857Notes

Reaction equation

HRID 926857 reaction equation
Cl[C:2]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[CH2:7][S:8][CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:3].N1C=CC=CC=1.[NH2:27][C:28]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:29]=1[C:30]([NH:32][C:33]1[CH:37]=[CH:36][N:35]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[C:40]([CH3:45])[CH:39]=2)[N:34]=1)=[O:31]>ClCCl>[Cl:50][C:47]1[CH:48]=[CH:49][C:28]([NH:27][C:2]([C:4]2[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=2)[CH2:7][S:8][CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:3])=[C:29]([C:30](=[O:31])[NH:32][C:33]2[CH:37]=[CH:36][N:35]([C:38]3[CH:43]=[CH:42][C:41]([CH3:44])=[C:40]([CH3:45])[CH:39]=3)[N:34]=2)[CH:46]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 665874962-amino-5-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)benzamideHCID 86705208Tert-butyl 3-(3-(chlorocarbonyl)benzylthio)propanoate

Product 1

HCID 66587776tert-butyl 3-(3-(4-chloro-2-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl-carbamoyl)phenylcarbamoyl)benzylthio)propanoateYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 50-mL round bottom flask, was placed a solution of tert-butyl 3-(3-(chlorocarbonyl)benzylthio)propanoate (185 mg, 0.59 mmol, 1.00 equiv) in dichloromethane (10 mL), and pyridine (140 mg, 1.77 mmol, 3.00 equiv). This was followed by dropwise addition of a solution of 2-amino-5-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)benzamide (200 mg, 0.59 mmol, 1.00 equiv) in dichloromethane (2 mL) with stirring. The resulting solution was stirred for 1 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (10:1) to yield 150 mg (33%) of product as a yellow solid.

Workup

  1. customInto a 50-mL round bottom flask, was placed
  2. stirringThe resulting solution was stirred for 1 h at room temperature
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. washeluted with petroleum ether/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-4cf9d261ef424cce90980d188eb4e4d6
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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