Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → Methyl 2-(6-(3-chlorophenyl)picolinamido)-2-methylpropanoate

HRID 631945Notes

Reaction equation

HRID 631945 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[NH2:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]([NH:21][C:20]([CH3:23])([CH3:22])[C:19]([O:18][CH3:17])=[O:24])=[O:16])[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 4186341Methyl 2-amino-2-methylpropanoateHCID 247301356-(3-Chlorophenyl)picolinic acid

Product 1

HCID 71087931Methyl 2-(6-(3-chlorophenyl)picolinamido)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(3-chlorophenyl)-2-pyridinecarboxylic acid (CAN 863704-38-5, 0.2 mmol), 2-methyl-alanine methyl ester (0.2 mmol) and HBTU (CAN 94790-37-1, 114 mg, 0.3 mmol) in DMF (0.5 mL) was stirred for 20 h at room temperature. The crude reaction mixture was concentrated in vacuo by centrifugation and purified by flash chromatography (silica gel, 20 g, 0% to 100% ethyl acetate in heptane) to give the desired product together with some impurities (73 mg, 116%) as light yellow oil; MS (LC/MS): 333.1 (M+H).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo by centrifugation
  3. custompurified by flash chromatography (silica gel, 20 g, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-1567794216904e0a92c6d11720324954
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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