1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-oxo-2-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenylamino)-1-((R)-3-oxo-4-(4-(trifluoromethyl)phenyl)morpholin-2-yl)ethyl acetate

HRID 876602Notes

Reaction equation

HRID 876602 reaction equation
[C:1]([O:4][C@H:5]([C@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[C:10]1=[O:25])[C:6](O)=[O:7])(=[O:3])[CH3:2].[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[NH:34][O:35][C:36](=[O:38])[N:37]=2)=[CH:29][CH:28]=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CC#N>[C:1]([O:4][C@H:5]([C@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=2)[C:10]1=[O:25])[C:6](=[O:7])[NH:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[NH:37][C:36](=[O:38])[O:35][N:34]=2)=[CH:31][CH:32]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58181429HCID 58181429, compoundHCID 178507458HCID 178507458, compound

Product 1

HCID 136009057(R)-2-oxo-2-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenylamino)-1-((R)-3-oxo-4-(4-(trifluoromethyl)phenyl)morpholin-2-yl)ethyl acetateYield 42.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of compound 93-3 (175 mg, 0.50 mmol), DMAP (12 mg, 20 mmol %), and 3-(4-aminophenyl)-1,2,4-oxadiazol-5(2H)-one 1 (177 mg, 2 eq) in MeCN (2.5 ml) at 0° C., EDCI (191 mg, 2 eq) was added. The resulting mixture was stirred at RT for 2 h. The volatile materials were removed on the rotavap. The residue was purified by silica gel chromatography (MeOH/DCM 0 to 10%) to give compound 96-1 (110 mg).

Workup

  1. customThe volatile materials were removed on the rotavap
  2. customThe residue was purified by silica gel chromatography (MeOH/DCM 0 to 10%)

Sources & evidence

ORD record
ord-308c09de56fe41d6b55aa3050cc187b5
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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