4-Fluorobenzenesulfonyl chloride → HCID 44217943, compound

HRID 1931484Notes

Reaction equation

HRID 1931484 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C@H:13]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]1)[CH:6]=[CH:5]2.[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([NH:12][C@H:13]2[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][CH2:14]2)[CH:6]=[CH:5]3)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 44217943HCID 44217943, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(6-Amino-quinolin-2-yl)-(R)-indan-1-yl-amine (0.05 g, 0.18 mmol) and 4-fluoro-benzenesulfonyl chloride (0.035 g, 0.18 mmol) were dissolved in pyridine (1 mL). The reaction mixture was stirred for 16 h at ambient temperature. Saturated sodium bicarbonate solution was added then and the aqueous phase extracted with ethyl acetate (3×10 mL). The combined organic phases were dried over sodium sulfate, filtered and the filtrate was evaporated. The residual oil was subjected to column chromatography (silica gel, heptane, ethyl acetate; 9:1=>1:1) to yield the title compound as a brown solid (5 mg, 6%); MS 434.7 [(M+H)+].

Workup

  1. extractionthe aqueous phase extracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-15f089c29af040f1a312ab92baec15f4
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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