1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 2-(4-(4'-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881727Notes

Reaction equation

HRID 881727 reaction equation
[CH:1]1([C:5]([NH:7][NH:8][C:9](=S)[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34][CH3:35])=[O:33])([CH2:27][CH2:28]4)[O:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH:1]1([C:5]2[O:6][C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]56[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34][CH3:35])=[O:33])([CH2:27][CH2:28]5)[O:25][CH2:24]6)=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)=[N:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86700833Methyl 2-(4-(4'-(2-(cyclobutanecarbonyl) hydrazinecarbothioamido) biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Product 1

HCID 86700834Methyl 2-(4-(4'-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a reaction vial containing methyl 2-(4-(4′-(2-(cyclobutanecarbonyl)hydrazinecarbothioamido) biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (300 mg, 0.59 mmol) was added DCM (6 ml) at room temperature. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (204 mg, 1.06 mmol) was added and the mixture was stirred at room temperature for overnight. The reaction mixture was purified directly via column chromatography affording the title compound as off-white solid after drying (252 mg, 90% yield). LC/MS, ESI-MS(+): 474.4, RT: 1.40 (Condition E).

Workup

  1. customThe reaction mixture was purified directly via column chromatography

Sources & evidence

ORD record
ord-df603e5309844ee88e1574a173f87aa3
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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