Methanone, (3-aminophenyl)phenyl- → 2-(4-Adamantan-1-yl-phenoxy)-N-(3-benzoyl-phenyl)-acetamide

HRID 1945401Notes

Reaction equation

HRID 1945401 reaction equation
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:22][C:23]1[CH:24]=[C:25]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])[CH:26]=[CH:27][CH:28]=1.Cl.C(N=C=N)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29](=[O:30])[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:24]=4)=[O:18])=[CH:13][CH:12]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

7

Reactant 5

HCID 17817Methanone, (3-aminophenyl)phenyl-HCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8HCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 248113272-(4-Adamantan-1-yl-phenoxy)-N-(3-benzoyl-phenyl)-acetamideYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the (4-adamantan-1-yl-phenoxy)-acetic acid (143 mg, 0.5 mmol) and (3-amino-phenyl)phenyl-methanone (148 mg, 0.75 mmol) in DMF (5.0 mL) were added 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (144.0 mg, 0.75 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (101 mg, 0.75 mmol), and N,N-diisopropylethylamine (DIPEA) (0.13 ml, 0.75 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. Purification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=12:3:1) gave 2-(4-Adamantan-1-yl-phenoxy)-N-(3-benzoyl-phenyl)-acetamide as a white solid (173.1 mg, 74.3% yield).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=12:3:1)

Sources & evidence

ORD record
ord-79ee9062cdb946c79e4a3a5129e69a89
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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