2-Aminopyridine → HCID 58552831, compound

HRID 520451Notes

Reaction equation

HRID 520451 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:4](=[O:6])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

8

Reactant 4

HCID 104392-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27948122-amino-3-(methoxycarbonyl)benzoic acid

Product 1

HCID 58552831HCID 58552831, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-3-(methoxycarbonyl)benzoic acid 20 (1 g, 5.1 mmol), 2-aminopyridine 21 (723 mg, 7.7 mmol), HOBT (1.39 g, 10.3 mmol), EDCI (1.9 g, 10.3 mmol) and DMAP (1.25 g, 10.3 mmol) in DMF (40 mL) was stirred at 70° for 12 h. The reaction mixture was poured into H2O. The resulting precipitate was collected by filtration, rinsed with H2O, and dried under vacuum to give 22 (0.9 g, 58% yield).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washrinsed with H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-777a2e4098624d8abbfb619c1be6375d
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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