Methanol → HCID 24779732, compound

HRID 1945452Notes

Reaction equation

HRID 1945452 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[N:31]=[CH:30][CH:29]=[CH:28][C:24]=1C(N)=O.C1CN([P+](ON2N=[N:56][C:51]3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C[OH:66]>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]([NH:22][C:23]4[CH:24]=[C:28]([CH:29]=[CH:30][N:31]=4)[C:51]([NH2:56])=[O:66])=[O:18])=[CH:20][CH:21]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

7

Reactant 4

HCID 887MethanolHCID 5066232-Aminopyridine-3-carboxamideHCID 625381PMID26882240-Compound-8HCID 2724699PyBOP

Product 1

HCID 24779732HCID 24779732, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To solution of (4-adamantan-1-yl-phenoxy)acetic acid (70 mg, 0.24 mmol), 2-amino nicotinamide (50.28 mg, 0.36 mmol) and DMAP (59.77 mg, 0.48 mmol) in DMF 5 ml was added PyBOP (452 mg, 0.86 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 PLC (EtoAC:Hexane:MeOH=3:6:1-2:4:1) to afford 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.05 g, 50% 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 PLC (EtoAC:Hexane:MeOH=3:6:1-2:4:1)

Sources & evidence

ORD record
ord-62f60618e57448d29d050e96c2b4edb6
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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