4-Methylmorpholine → Methyl 6-(6-cyclopropyl-3,4'-bipyridine-2'-carboxamido)picolinate

HRID 389626Notes

Reaction equation

HRID 389626 reaction equation
Cl.[CH:2]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([C:17]([OH:19])=O)[CH:12]=3)=[CH:7][CH:6]=2)[CH2:4][CH2:3]1.[CH3:20][O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[N:24]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH:2]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH:29][C:25]4[N:24]=[C:23]([C:22]([O:21][CH3:20])=[O:30])[CH:28]=[CH:27][CH:26]=4)=[O:19])[CH:12]=3)=[CH:7][CH:6]=2)[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13809143Methyl 6-aminopyridine-2-carboxylateHCID 668490066-Cyclopropyl-3,4'-bipyridine-2'-carboxylic acid hydrochloride salt

Product 1

HCID 66848750Methyl 6-(6-cyclopropyl-3,4'-bipyridine-2'-carboxamido)picolinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-cyclopropyl-3,4′-bipyridine-2′-carboxylic acid hydrochloride salt (1.73 g, 6.25 mmol), 6-aminopicolinate methyl ester (1.05 g, 6.87 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 2.85 g, 7.50 mmol), and N-methylmorpholine (1.51 mL, 13.8 mmol) in N,N-dimethylformamide was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure, and the residue suspended in acetonitrile. The solid thus obtained was isolated by filtration, washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL) and dried under reduced pressure to afford methyl 6-(6-cyclopropyl-3,4′-bipyridine-2′-carboxamido)picolinate as a white powder, which was used directly in the next step.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe solid thus obtained
  3. customwas isolated by filtration
  4. washwashed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8c1ce16f4ec84cb5b2a6f938612f18dd
Source dataset
uspto-grants-2013_02
Patent number
US08378108B2

Reaction notes

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