Benzyl mercaptan → (S)-tert-Butyl (3-(benzylthio)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

HRID 1052373Notes

Reaction equation

HRID 1052373 reaction equation
Br[CH2:2][CH2:3][C@H:4]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9](=[O:17])[C:8]2=[CH:18][CH:19]=[CH:20][N:7]2[N:6]=1.[CH2:29]([SH:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH2:29]([S:36][CH2:2][CH2:3][C@H:4]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9](=[O:17])[C:8]2=[CH:18][CH:19]=[CH:20][N:7]2[N:6]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 131736118(S)-tert-Butyl (3-bromo-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

Product 1

HCID 131736120(S)-tert-Butyl (3-(benzylthio)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamateYield 81.5%

Procedure

(S)-tert-Butyl (3-bromo-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate (45 mg, 0.03 mmol) was treated with benzyl hydrosulfide (7 μl, 0.06 mmol) and potassium carbonate (6 mg, 0.05 mmol) according to the method described in Preparation 31. The residue was purified using SP1® Purification System (0% to 50%, hexane-ethyl acetate) to give 12 mg (81% yield) of the title compound. Purity 70%.

Workup

  1. customdescribed in Preparation 31
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 50%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4ee43ef58d614642843295797e10bf98
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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