Triethylamine → HCID 178462103, compound

HRID 1040542Notes

Reaction equation

HRID 1040542 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3=[N:14][CH:15]=[C:16]([C:17]([NH:19][C@@H:20]([CH3:24])[C:21]([OH:23])=O)=[O:18])[N:12]3[C@@:11]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[CH:29][CH:28]=3)([CH3:25])[C:10]2=[O:40])[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O.[NH:48]1[C:52]([C@@H:53]2[CH2:58][CH2:57][CH2:56][NH:55][CH2:54]2)=[N:51][N:50]=[N:49]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>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[C:10](=[O:40])[C@:11]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:33]4[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=4)=[CH:31][CH:32]=3)([CH3:25])[N:12]3[C:16]([C:17]([NH:19][C@@H:20]([CH3:24])[C:21](=[O:23])[N:55]4[CH2:56][CH2:57][CH2:58][C@@H:53]([C:52]5[NH:51][N:50]=[N:49][N:48]=5)[CH2:54]4)=[O:18])=[CH:15][N:14]=[C:13]23)[CH:3]=[C:2]([Cl:1])[CH:7]=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 58431048(S)-2-{[(R)-7-(3,5-dichloro-phenyl)-5-(4'-fluoro-biphenyl-4-ylmethyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acidHCID 178420791HCID 178420791, compound

Product 1

HCID 178462103HCID 178462103, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of (S)-2-{[(R)-7-(3,5-dichloro-phenyl)-5-(4′-fluoro-biphenyl-4-ylmethyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid (0.12 g, 0.21 mmol) in DMF (1 mL) was added (R)-3-(1H-tetrazol-5-yl)-piperidine trifluoro-acetic acid salt (0.055 g, 0.21 mmol), HATU (0.093 mg, 0.25 mmol) and Et3N (0.059 mL, 0.41 mmol). The reaction was allowed to stir for 10 min and then HOAt (0.056 g, 0.41 mmol) was added. The mixture was allowed to warm to room temperature overnight. The crude reaction mixture was purified by reverse phase HPLC to give 35 mg of the title compound as a white solid, m/z 716.6 [M]+.

Workup

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

Sources & evidence

ORD record
ord-2e840c37c2b84c63895e945b480f2798
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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