Diisopropylethylamine → HCID 60197097, compound

HRID 877967Notes

Reaction equation

HRID 877967 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](Cl)=[O:6].[CH3:12][NH:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([N:13]([CH3:12])[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1456003,5-Difluorobenzoyl chlorideHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 60197097HCID 60197097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Difluorobenzoyl chloride (50 mg, 0.28 mmol, CAS RN 129714-97-2) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (45 mg, 0.23 mmol, example 1, intermediate a) and DIPEA (79 μL, 0.45 mmol) in CH2Cl2 (1 mL). The reaction mixture was stirred overnight and then loaded directly onto a silica gel column and eluted with 50% EtOAc in n-hexane to yield the desired compound as a waxy solid (26 mg, 34%). MS (ESI): m/z=339.1 [M+H]+.

Workup

  1. washeluted with 50% EtOAc in n-hexane

Sources & evidence

ORD record
ord-33dddce996e4482b95b413f8c75edd5f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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