Triethylamine → HCID 86728470, compound

HRID 2170415Notes

Reaction equation

HRID 2170415 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([F:12])[CH:4]=1)#[N:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:37][O:38][C:39]1[CH:44]=[C:43]([NH2:45])[CH:42]=[CH:41][N:40]=1.CCN(CC)CC>ClCCl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:45][C:43]2[CH:42]=[CH:41][N:40]=[C:39]([O:38][CH3:37])[CH:44]=2)=[O:9])=[C:5]([F:12])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2808912-Methoxypyridin-4-amineHCID 5906594-Cyano-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 86728470HCID 86728470, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-cyano-2-fluoro-benzoic acid (6.7 g, 40.58 mmol), HATU (15.4 g, 40.58 mmol), 2-methoxypyridin-4-amine (5.0 g, 40.58 mmol) and Et3N (22.62 mL, 162.3 mmol) in dichloromethane (60.3 mL) was stirred at room temperature overnight. The crude mixture was purified by column chromatography using a gradient of ethyl acetate in hexanes (0-50%) to yield 4-cyano-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (7.3 g, 66%) as a white solid. ESI-MS m/z calc. 271.07. found 272.1 (M+1)+; Retention time: 1.17 minutes (3 minutes run).

Workup

  1. customThe crude mixture was purified by column chromatography

Sources & evidence

ORD record
ord-e46f22a19e63404c860d39952685c3cd
Source dataset
uspto-grants-2015_06
Patent number
US09051270B2

Reaction notes

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