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

HRID 1052370Notes

Reaction equation

HRID 1052370 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.C(N(CC)CC)C.O[CH2:30][CH2:31][C@H:32]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[C:33]1[N:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:37](=[O:45])[C:36]2=[CH:46][CH:47]=[CH:48][N:35]2[N:34]=1>ClCCl.O>[Br:20][CH2:30][CH2:31][C@H:32]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[C:33]1[N:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:37](=[O:45])[C:36]2=[CH:46][CH:47]=[CH:48][N:35]2[N:34]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 24408BromineHCID 131736117(S)-tert-Butyl (3-hydroxy-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

Product 1

HCID 131736118(S)-tert-Butyl (3-bromo-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamateYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (170 mg, 0.44 mmol) was dissolved in 2 mL anhydrous dichloromethane. Bromine (32 μl, 0.62 mmol) was added dropwise under argon atmosphere and the reaction was stirred at room temperature for 30 min. Triethylamine (247 μl, 1.77 mmol) and (S)-tert-butyl (3-hydroxy-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate (170 mg, 0.44 mmol) were added and the reaction mixture was stirred at room temperature for 2 h. The mixture was poured into water and extracted with dichlorometane. The organics were dried over sodium sulphate, filtered and evaporated. The residue purified using SP1® Purification System (0% to 30%, hexane-ethyl acetate) to obtain 147 mg (74% yield) of the title compound as a white solid. Purity 100%.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. extractionextracted with dichlorometane
  3. dry with materialThe organics were dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue purified
  7. customSP1® Purification System (0% to 30%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-28d0de49fee445eeb93cdbd63e02eeec
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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