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

HRID 2170411Notes

Reaction equation

HRID 2170411 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[CH:3]=1.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:10]=[CH:9][C:5]([C:6]([NH:44][C:42]2[CH:41]=[CH:40][N:39]=[C:38]([O:37][CH3:36])[CH:43]=2)=[O:8])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 991524-Chloro-2-fluorobenzoic acidHCID 2808912-Methoxypyridin-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 867284664-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamideYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-2-fluoro-benzoic acid (7.0 g, 40.10 mmol), HATU (15.25 g, 40.10 mmol), 2-methoxypyridin-4-amine (4.98 g, 40.10 mmol) and Et3N (22.4 mL, 160.4 mmol) in dichloromethane (63.0 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 4-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (4.35 g, 39%), as a white solid. ESI-MS m/z calc. 280.04. found 281.3 (M+1)+; Retention time: 1.31 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 10.80 (s, 1H), 8.09 (m, 1H), 7.73 (t, J=8.0 Hz, 1H), 7.66 (dd, J=10.1, 1.9 Hz, 1H), 7.46 (dd, J=8.3, 1.9 Hz, 1H), 7.21 (m, 2H), 3.84 (s, 3H) ppm.

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-4c066c915b6e40dca6884856a7060e0e
Source dataset
uspto-grants-2015_06
Patent number
US09051270B2

Reaction notes

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