Methyl 2-aminopyridine-4-carboxylate → HCID 24811989, compound

HRID 1945428Notes

Reaction equation

HRID 1945428 reaction equation
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([OH:19])=O)=[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.[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([NH2:31])[CH:26]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:17](=[O:19])[CH2:16][O:15][C:14]2[CH:20]=[CH:21][C:11]([C:1]34[CH2:8][CH:7]5[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]5)[CH2:2]3)[CH2:10]4)=[CH:12][CH:13]=2)[CH:26]=1

Participants

7

Reactant 3

HCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 625381PMID26882240-Compound-8HCID 2724699PyBOP

Product 1

HCID 24811989HCID 24811989, compoundYield 75.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of appropriate (4-adamantan-1-yl-phenoxy)-acetic acid (150 mg, 0.523 mmol), 2-amino isonicotinic acid methyl ester (159.3 mg, 1.04 mmol) and DMAP (127.9 mg, 1.04 mmol) in DMF (6 ml) was added PyBOP (545 mg, 1.04 mmol) at room temperature and the resulting mixture was stirred until reaction completion as indicated by TLC. Reaction mixture was poured onto ice cold water, diluted with ethyl acetate, separated organic layer and sequentially washed with aqueous sodium bicarbonate, brine and water, and dried over anhydrous MgSO4. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by flash chromatography on silica gel (EtOAc:hexanes=1:9 to 1:1) to afford of 2-[2-(4-adamantan-1-yl-phenoxy)acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.166 g, 75% yield).

Workup

  1. customReaction mixture
  2. additionwas poured onto ice cold water
  3. customseparated organic layer
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationThe solvent was filtered
  7. customevaporated under reduced pressure
  8. customto afford a crude solid, which
  9. customwas purified by flash chromatography on silica gel (EtOAc:hexanes=1:9 to 1:1)

Sources & evidence

ORD record
ord-d902aca7166240b39eb5f6d4dc86bfaa
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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