3-Aminobenzonitrile → HCID 54523328, compound

HRID 1945396Notes

Reaction equation

HRID 1945396 reaction equation
C12(C3C=C[C:14]([O:15]CC(O)=O)=[CH:13]C=3)CC3CC(CC(C3)C1)C2.N[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27].O[N:32]1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:26]([C:25]1[CH:24]=[C:23]([CH2:13][C:14]([NH2:32])=[O:15])[CH:30]=[CH:29][CH:28]=1)#[N:27]

Participants

6

Reactant 4

HCID 167023-AminobenzonitrileHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8

Product 1

HCID 54523328HCID 54523328, compoundYield 198.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-(4-Adamantan-1-yl-phenoxy)-acetic acid (200.0 mg, 0.70 mmol), 3-amino-benzonitrile (124.1 mg, 1.05 mmol), N-(3-dimethylaminopropyl)-N-ethyl carbodiimide HCl (EDC) (201.3 mg, 1.05 mmol) and 1-hydroxybenzotriazole (HOBt) (142.9 mg, 1.05 mmol) in DMF (10 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (131.5 mg, 0.18 ml, 1.05 mmol). The mixture was stirred overnight; and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:EtoAc:MeOH=6:3:1) to give 2-(4-Adamantyl-1-yl-phenoxyl)-N-(3-cyano-phenylacetamide as a yellow solid (222.8 mg, 82.6% yield).

Workup

  1. distillationredistilled (DIPEA) (131.5 mg, 0.18 ml, 1.05 mmol)
  2. customand then partitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-c72fcc0c09b9455faf464156a8ed265f
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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