Triethylamine → Methyl 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinate

HRID 923553Notes

Reaction equation

HRID 923553 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:42][C:43]1[CH:44]=[CH:45][C:46]([C:49]([O:51][CH3:52])=[O:50])=[N:47][CH:48]=1.C(N(CC)CC)C>CN(C=O)C.CC(=O)OCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:42][C:43]2[CH:44]=[CH:45][C:46]([C:49]([O:51][CH3:52])=[O:50])=[N:47][CH:48]=2)=[O:12])=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 467375752-(4-Methoxy-2-(trifluoromethyl)phenyl)acetic acidHCID 73554701Methyl 5-aminopicolinate hydrochloride

Product 1

HCID 71076831Methyl 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinateYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared using General Procedure 6: To a stirred solution of 2-(4-methoxy-2-(trifluoromethyl)phenyl)acetic acid (200 mg, 0.85 mmol), HATU (210 mg, 0.89 mmol) in DMF (5 mL) was added methyl 5-aminopicolinate hydrochloride (156 mg, 1.02 mmol) followed by triethylamine (226 mg, 2.24 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with EA (10 mL) and washed with NaHCO3 (10 mL), NH4Cl (10 mL) and brine (10 mL) then dried over MgSO4 and concentrated to give 78 mg (25%) of methyl 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinate INT-14 which was used in the next step without purification. LCMS-ESI (m/z) calculated C17H15F3N2O4: 368; found 369 [M+H]+, tR=3.06 min (Method 1).

Workup

  1. customPrepared
  2. washwashed with NaHCO3 (10 mL), NH4Cl (10 mL) and brine (10 mL)
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7c8c1ac0dcb64892a4c3c6c020664199
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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