Triethylamine → 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide

HRID 2170413Notes

Reaction equation

HRID 2170413 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:36][O:37][C:38]1[CH:43]=[C:42]([NH2:44])[CH:41]=[CH:40][N:39]=1.CCN(CC)CC>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:44][C:42]1[CH:41]=[CH:40][N:39]=[C:38]([O:37][CH3:36])[CH:43]=1)=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2808912-Methoxypyridin-4-amineHCID 27365375-Chloro-2-fluorobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 867284685-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamideYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-2-fluoro-benzoic acid (5.0 g, 28.64 mmol), HATU (10.89 g, 28.64 mmol), 2-methoxypyridin-4-amine (3.6 g, 28.64 mmol) and Et3N (15.98 mL, 114.60 mmol) in dichloromethane (45.0 mL) was stirred at room temperature overnight. The crude mixture was purified by column chromatography eluting with a gradient of ethyl acetate in hexanes (0-50%) to yield 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (3.8 g, 47%) as a white solid. ESI-MS m/z calc. 280.04. found 281.3 (M+1)+; Retention time: 1.31 minutes (3 minutes run).

Workup

  1. customThe crude mixture was purified by column chromatography
  2. washeluting with a gradient of ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-dc2dac72505b41d18c3a24cf0798d3b7
Source dataset
uspto-grants-2015_06
Patent number
US09051270B2

Reaction notes

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