Triethylamine → HCID 178462102, compound

HRID 1040539Notes

Reaction equation

HRID 1040539 reaction equation
[Br:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C@@:7]2([CH3:32])[N:11]3[C:12]([C:15]([NH:17][C@@H:18]([CH3:22])[C:19]([OH:21])=O)=[O:16])=[CH:13][N:14]=[C:10]3[N:9]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)[C:8]2=[O:31])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[NH:42]1[C:46]([C@@H:47]2[CH2:52][CH2:51][CH2:50][NH:49][CH2:48]2)=[N:45][N:44]=[N:43]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[Br:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C@@:7]2([CH3:32])[N:11]3[C:12]([C:15]([NH:17][C@@H:18]([CH3:22])[C:19](=[O:21])[N:49]4[CH2:50][CH2:51][CH2:52][C@@H:47]([C:46]5[NH:45][N:44]=[N:43][N:42]=5)[CH2:48]4)=[O:16])=[CH:13][N:14]=[C:10]3[N:9]([C:23]3[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=3)[C:8]2=[O:31])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58431145(S)-2-{[(R)-5-(4-bromo-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acidHCID 178420791HCID 178420791, compound

Product 1

HCID 178462102HCID 178462102, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of (S)-2-{[(R)-5-(4-bromo-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid (0.050 g, 0.088 mmol) in DMF (1 mL) was added (R)-3-(1H-tetrazol-5-yl)-piperidine trifluoro-acetic acid salt (0.047 g, 0.18 mmol), HATU (0.040 g, 0.11 mmol) and Et3N (0.026 mL, 0.18 mmol). The reaction was allowed to stir for 10 minutes and HOAt (0.024 g, 0.18 mmol) was added and the mixture allowed to warm to room temperature overnight. The crude reaction mixture was purified by reverse-phase HPLC to give 10 mg of the title compound as a white solid, m/z 701.4 [M]+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-6a9e394a8ad94e1ebf40d8fa288c8319
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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