Potassium Carbonate → (S)-tert-Butyl (1-(5-((3-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

HRID 1052424Notes

Reaction equation

HRID 1052424 reaction equation
I[C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=[N:6]2.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([SH:36])[CH:33]=[CH:34][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([S:36][C:2]2[CH:3]=[CH:4][N:5]3[C:10]=2[C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=[N:6]3)[CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 849893-MethoxybenzenethiolHCID 131736123HCID 131736123, compound

Product 1

HCID 131736152(S)-tert-Butyl (1-(5-((3-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamateYield 30%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

(S)-tert-Butyl (1-(5-iodo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (500 mg, 1.04 mmol) was treated with 3-methoxybenzenethiol (219 mg, 1.56 mmol), potassium carbonate (216 mg, 1.56 mmol) and copper(I) iodide (297 mg, 1.56 mmol) according to the method described in Preparation 44. The residue was purified by reverse phase using Isolera® Purification System to give 154 mg (30% yield) to the title compound. Purity 100%.

Workup

  1. customdescribed in Preparation 44
  2. customThe residue was purified by reverse phase
  3. customIsolera® Purification System

Sources & evidence

ORD record
ord-f00c513f991445a4b69cb69c68f078d6
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…