1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Benzyl 2-(5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-((3-(trifluoromethoxy)benzamido)methyl)phenylamino)acetate

HRID 1296764Notes

Reaction equation

HRID 1296764 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([CH3:15])[O:12][N:11]=2)=[CH:6][C:5]=1[NH:16][CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[F:49][C:50]([F:62])([F:61])[O:51][C:52]1[CH:53]=[C:54]([CH:58]=[CH:59][CH:60]=1)[C:55](O)=[O:56]>ClCCl.CN(C=O)C>[CH3:15][C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][NH:2][C:55](=[O:56])[C:54]3[CH:58]=[CH:59][CH:60]=[C:52]([O:51][C:50]([F:49])([F:61])[F:62])[CH:53]=3)=[C:5]([NH:16][CH2:17][C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[CH:6]=2)[N:14]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 660963-(Trifluoromethoxy)benzoic acidHCID 181649HOAtHCID 69490392Benzyl 2-(2-(aminomethyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)acetate hydrochloride

Product 1

HCID 69491528Benzyl 2-(5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-((3-(trifluoromethoxy)benzamido)methyl)phenylamino)acetateYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 58d (50 mg, 0.13 mmol), TEA (0.027 mL), HOAt (1.8 mg) and EDCI (37 mg, 0.19 mmol) in a mixture of dichloromethane (0.8 mL) and DMF (0.3 mL) was added 3-trifluoromethoxybenzoic acid (27 mg, 0.13 mmol). The resulting solution was stirred overnight at rt, and then concentrated. The residue was triturated with water, and then purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.1% TFA) to afford compound 58e (30 mg, 43%). ESI-MS m/e 541.4 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with water
  3. custompurified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.1% TFA)

Sources & evidence

ORD record
ord-4e681782f40e4578b14b6ca68c7bd33d
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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