Triethylamine → (S)-tert-Butyl (3-(benzyloxy)-1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

HRID 1052393Notes

Reaction equation

HRID 1052393 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:12]([NH:14][N:15]1[CH:19]=[CH:18][C:17]([Br:20])=[C:16]1[C:21](=[O:29])[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrBr.C(N(CC)CC)C.C[S-].[Na+]>>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:12]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:21](=[O:29])[C:16]2=[C:17]([Br:20])[CH:18]=[CH:19][N:15]2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 24408BromineHCID 4378561Sodium methanethiolateHCID 131736129(S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamate

Product 1

HCID 131736130(S)-tert-Butyl (3-(benzyloxy)-1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamateYield 90.3%

Procedure

(S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamate (0.7 g, 1.22 mmol) was treated with triphenylphosphine (0.45 g, 1.72 mmol), bromine (88 μl, 1.72 mmol), triethylamine (683 μl, 4.90 mmol) and sodium methanethiolate (0.17 g, 2.45 mmol) according to the method of Preparation 23. The residue was purified using Isolera® Purification System (0% to 20%, hexane-ethyl acetate) to give 0.61 g (90% yield) of the title compound. Purity 100%.

Workup

  1. customaccording to the method of Preparation 23
  2. customThe residue was purified
  3. customIsolera® Purification System (0% to 20%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-89d2484efba54e83846ec588261ac2a5
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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