Tetrahydrofuran → HCID 56963340, compound

HRID 922037Notes

Reaction equation

HRID 922037 reaction equation
[CH2:1]([S:3][C:4]1[C:9]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[O:11])=[C:8]([CH3:21])[CH:7]=[C:6]([NH:22][CH3:23])[N:5]=1)[CH3:2].C1COCC1.CCN(C(C)C)C(C)C.[F:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1>C(Cl)Cl.CCOC(C)=O>[CH2:1]([S:3][C:4]1[C:9]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[O:11])=[C:8]([CH3:21])[CH:7]=[C:6]([N:22]([C:43](=[O:44])[C:42]2[CH:46]=[CH:47][C:39]([F:38])=[CH:40][CH:41]=2)[CH3:23])[N:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 67287071HCID 67287071, compound

Product 1

HCID 56963340HCID 56963340, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 150 mg (0.45 mmol) 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-(methyl-amino)-4-methyl-pyridine-3-carboxylic acid amide (synthesis is described in section a) of example 123) in DCM (3 ml) and THF (3 ml) was added 160 μl (0.95 mmol) DIPEA. At 0° C. 56 μl (0.47 mmol) 4-fluoro-benzoylchloride was added dropwise and stirring was continued at 0° C. for 2 h and RT for 16 h. Then the mixture was partiotionated between EtOAc and a 1M aq. NaHCO3 sol. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 1:1) provided 171 mg (0.38 mmol, 83%) 2-Ethylsulfanyl-6-[(4-fluoro-benzoyl)-methyl-amino]-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide (example 120). [M+H]+ 456.1

Workup

  1. customAt 0° C
  2. customa 1M aq. NaHCO3 sol. The organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-4a1ef85a1ffc44baa3ff50aa01ffdb2d
Source dataset
uspto-grants-2016_03
Patent number
US09278103B2

Reaction notes

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