Methanol → 5-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-nicotinamide

HRID 1945451Notes

Reaction equation

HRID 1945451 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]=[N:25][CH:26]=[C:27]([CH:31]=1)[C:28]([NH2:30])=[O:29].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CO>CN(C1C=CN=CC=1)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:24]=[N:25][CH:26]=[C:27]([CH:31]=4)[C:28]([NH2:30])=[O:29])=[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 4

HCID 887MethanolHCID 1737473-Pyridinecarboxamide, 5-amino-HCID 625381PMID26882240-Compound-8HCID 2724699PyBOP

Product 1

HCID 444432625-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-nicotinamideYield 61.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To solution of (4-adamantan-1-yl-phenoxy)-acetic acid (50 mg, 0.17 mmol), 5-amino nicotinamide (47.89 mg, 0.34 mmol) and DMAP (42.71 mg, 0.34 mmol) in DMF 5 ml was added PyBOP (181 mg, 0.34 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by preparative-TLC(CH2Cl2:MeOH=6:1) to afford 5-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-nicotinamide as a colorless solid (42.48 mg, 60% yield).

Workup

  1. customReaction mixture
  2. additionwas poured onto ice cold water
  3. customThe organic phase was separated
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by preparative-TLC(CH2Cl2:MeOH=6:1)

Sources & evidence

ORD record
ord-e31ee4cd4d2e4ba482ec8db65f93a4ee
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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