Ethylamine hydrochloride → Methyl 4-(ethylcarbamoyl)picolinate

HRID 623569Notes

Reaction equation

HRID 623569 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][N:13]=1)[C:8]([OH:10])=O)=[O:4].Cl.[CH2:15]([NH2:17])[CH3:16].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:15]([NH:17][C:8]([C:7]1[CH:11]=[CH:12][N:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=1)=[O:10])[CH3:16]

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 187533102-(Methoxycarbonyl)pyridine-4-carboxylic acid

Product 1

HCID 67510192Methyl 4-(ethylcarbamoyl)picolinateYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(methoxycarbonyl)isonicotinic acid (150 mg, 0.83 mmol), ethylamine hydrochloride salt (203 mg, 2.48 mmol), and diisopropylethylamine (0.72 mL, 4.14 mmol) in DMF is added HBTU (377 mg, 0.99 mmol) at 0° C. After stirring at room temperature for 1 hour, the mixture is poured onto water (30 mL). The aqueous phase is extracted with dichloromethane (30 mL×2). The combined organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1˜1:1) to give 83 mg (48% yield) of the title compound as a white solid.

Workup

  1. additionthe mixture is poured onto water (30 mL)
  2. extractionThe aqueous phase is extracted with dichloromethane (30 mL×2)
  3. dry with materialThe combined organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1˜1:1)

Sources & evidence

ORD record
ord-aa3a302af7f14c068e0444ff9a7a3d5b
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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