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

HRID 1052368Notes

Reaction equation

HRID 1052368 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:12](=O)[NH:13][N:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](=[O:27])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[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.N>>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:12]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:19](=[O:27])[C:15]2=[CH:16][CH:17]=[CH:18][N:14]2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 24408BromineHCID 86722052(S)-tert-Butyl 4-(benzyloxy)-1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)butan-2-ylcarbamate

Product 1

HCID 131736116(S)-tert-Butyl (3-(benzyloxy)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamateYield 53.5%

Procedure

(S)-tert-Butyl (4-(benzyloxy)-1-oxo-1-((2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)butan-2-yl)carbamate (1.57 g, 3.19 mmol) was treated with triphenylphosphine (1.17 g, 4.46 mmol), bromine (229 μl, 4.47 mmol), triethylamine (1.78 mL, 12.77 mmol) and a solution of ammonia solution (7M in methanol, 150 mL, 1000 mmol) according to the method of Preparation 5b. The residue was purified using SP1® Purification System (0% to 30%, hexane-ethyl acetate) to give 0.81 g (53.5%) of the title compound as a white solid. Purity 100%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 30%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-14c3a0a8234e4887a34565b028f2690c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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