Dimethylformamide → HCID 117737016, compound

HRID 1504525Notes

Reaction equation

HRID 1504525 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([S:21]([NH:24][C:25]4[N:26]=[N:27][CH:28]=[CH:29][CH:30]=4)(=[O:23])=[O:22])=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:31])[C:5]([O:9][CH3:10])=[N:6][C:7]=1Cl.[C:32]([CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)#[CH:33].C(NC(C)C)(C)C.CN(C=O)C>O.C(OCC)(=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([S:21]([NH:24][C:25]4[N:26]=[N:27][CH:28]=[CH:29][CH:30]=4)(=[O:22])=[O:23])=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:31])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[C:33]#[C:32][CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

10

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 136725CyclopentylacetyleneHCID 117737023HCID 117737023, compound

Product 1

HCID 117737016HCID 117737016, compoundYield 65.6%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
100 °C

Procedure

A RBF was charged with 1-(5,6-dichloro-2-methoxypyridin-3-yl)-2-oxo-N-(pyridazin-3-yl)-1,2-dihydroquinoline-6-sulfonamide (0.075 g, 0.157 mmol), ethynylcyclopentane (0.074 ml, 0.784 mmol), diisopropylamine (0.134 ml, 0.941 mmol), copper(i) iodide (2.66 μl, 0.078 mmol), tetrakis(triphenylphosphine)palladium(0) (0.018 g, 0.016 mmol), and DMF (0.784 ml). The reaction was stirred at 100° C. for 18 hrs. The mixture was diluted with water and Ethyl Acetate. The organic portion was collected, dried with sodium sulfate, filtered, and concentrated. The crude material was purified via column chromatography (RediSep Gold 40 g, gradient elution 10-75% [3:1 EtOAc/EtOH]:Heptane to give 1-(5-chloro-6-(cyclopentylethynyl)-2-methoxy-3-pyridinyl)-2-oxo-N-3-pyridazinyl-1,2-dihydro-6-quinolinesulfonamide (55 mg, 0.103 mmol, 65.4% yield) as an off-white solid. m/z (ESI) 536.0 (M+H)+.

Workup

  1. customThe organic portion was collected
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified via column chromatography (
  6. washRediSep Gold 40 g, gradient elution 10-75% [3:1 EtOAc/EtOH]

Sources & evidence

ORD record
ord-985ead44f0144ef68c0d3f16632badb6
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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