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

HRID 1052428Notes

Reaction equation

HRID 1052428 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.[SH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[OH:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[S:28][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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70718Phenol, o-mercapto-(6CI,7CI,8CI)HCID 131736123HCID 131736123, compound

Product 1

HCID 131736153(S)-tert-Butyl (1-(5-((2-hydroxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamateYield 64%

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 (250 mg, 0.52 mmol) was treated with 2-mercaptophenol (80 μl, 0.80 mmol), potassium carbonate (110 mg, 0.8 mmol) and copper(I) iodide (150 mg, 0.79 mmol) according to the method described in Preparation 44. The crude was purified using SP1® Purification System (0%-25%, hexane-ethyl acetate) to give 252 mg (64% yield) to the title compound as an oil.

Workup

  1. customdescribed in Preparation 44
  2. customThe crude was purified
  3. customSP1® Purification System (0%-25%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e4c7d494315c45e68fc9aa2acdea3ac5
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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