1-(1H-Imidazol-1-yl)ethanone → HCID 16747179, compound

HRID 20059

Reaction equation

HRID 20059 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:5]([OH:24])[CH2:6][NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[O:11][C:10]([CH3:23])([C:19]([F:22])([F:21])[F:20])[CH2:9]1.N1([C:37](=[O:39])[CH3:38])C=CN=C1.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[Br:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[O:11][C@:10]([CH3:23])([C:19]([F:22])([F:21])[F:20])[CH2:9][C@@H:8]2[NH:7][CH2:6][C@@H:5]([OH:24])[C@@H:4]([NH:3][C:37](=[O:39])[CH3:38])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 81531DiisopropylethylamineHCID 86614141(2R,3S)-3-amino-1-((4S)-6-bromo-2-methyl-2-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-ylamino)-4-phenylbutan-2-ol dihydrochloride

Product 1

HCID 16747179HCID 16747179, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R,3S)-3-amino-1-((4S)-6-bromo-2-methyl-2-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-ylamino)-4-phenylbutan-2-ol dihydrochloride (160 mg, 338 mmol) in DMF was added 1-(1H-imidazol-1-yl)ethanone (37.2 mg, 338 μmol) followed by DIPEA (177 μl, 1014 μmol). The reaction was stirred at RT for 30 min, then diluted with MeOH and purified on Shimadzu HPLC to afford 43.0 mg of the title compounds as a mixture. MS m/z: 515, 517.

Workup

  1. custompurified on Shimadzu HPLC

Sources & evidence

ORD record
ord-811784750c46412ea16a8463960b8434
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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