Triethylamine → HCID 58431203, compound

HRID 1040523Notes

Reaction equation

HRID 1040523 reaction equation
[C:1]([C:3]1[CH:35]=[CH:34][C:6]([CH2:7][C@@:8]2([CH3:33])[N:12]3[C:13]([C:16]([NH:18][C@@H:19]([CH3:23])[C:20]([OH:22])=O)=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)[C:9]2=[O:32])=[CH:5][CH:4]=1)#[N:2].[N:36]1[NH:37][N:38]=[N:39][C:40]=1[C@@H:41]1[CH2:46][CH2:45][CH2:44][NH:43][CH2:42]1.CCN(CC)CC.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([C:3]1[CH:35]=[CH:34][C:6]([CH2:7][C@@:8]2([CH3:33])[N:12]3[C:13]([C:16]([NH:18][C@@H:19]([CH3:23])[C:20](=[O:22])[N:43]4[CH2:44][CH2:45][CH2:46][C@@H:41]([C:40]5[N:36]=[N:37][NH:38][N:39]=5)[CH2:42]4)=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:24]3[CH:25]=[C:26]([Cl:31])[CH:27]=[C:28]([Cl:30])[CH:29]=3)[C:9]2=[O:32])=[CH:5][CH:4]=1)#[N:2]

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 58430990HCID 58430990, compoundHCID 58431091HCID 58431091, compound

Product 1

HCID 58431203HCID 58431203, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid (60 mg, 0.117 mmol) and (R)-3-(2H-tetrazol-5-yl)-piperidine (35.8 mg, 0.234 mmol) in anhydrous DMF (1 mL) was added Et3N (33.8 μl, 0.234 mmol) at 0° C. HOAt (47.8 mg, 0.351 mmol) was then added to the reaction. After 10 min of stirring at 0° C., HATU (53.4 mg, 0.140 mmol) was added. The reaction was slowly warmed to 25° C. and stirred overnight. The crude reaction was purified by reverse phase HPLC to afford 55 mg of (3R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-N-{(1S)-1-methyl-2-oxo-2-[(3R)-3-(2H-tetrazol-5-yl)piperidin-1-yl]ethyl}-2-oxo-2,3-dihydro-1H-imidazo[1,2-a]imidazole-5-carboxamide as a white solid, m/z 647.5 [M+1]+.

Workup

  1. temperatureThe reaction was slowly warmed to 25° C.
  2. stirringstirred overnight
  3. customThe crude reaction
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-397da7ec98cb47b1bc8bd458733a8da2
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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