Methanesulfonyl chloride → HCID 10665443, compound

HRID 977167Notes

Reaction equation

HRID 977167 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.F[C:21](F)(F)[S:22](O[Si](C(C)(C)C)(C)C)(=[O:24])=[O:23].CS(Cl)(=O)=O>O1CCCC1>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:1][S:22]([CH3:21])(=[O:24])=[O:23])=[C:3]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4](=[O:13])[NH:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 10707207HCID 10707207, compound

Product 1

HCID 10665443HCID 10665443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-amino-7-chloro-3-phenyl-2(1H)-quinolone (0.55 g, 2 mmol) (Example 2) and potassium (bistrimethylsilyl) amide (4 ml, 0.5M solution in toluene) in 50 ml tetrahydrofuran were stirred for 10 mins prior to the addition of tert-butyldimethylsilyl trifluoromethanesulfonate (6.1 ml). After a further 10 mins a further portion of potassium(bistrimethylsilyl)amide (6.1 ml) was added followed after 10 mins by methanesulfonyl chloride (0.48 ml). The solvent was removed in vacuo after one hour and the residue was suspended in 5N HCl (30 ml), and treated with ultrasound for 5 mins before being filtered. The solid was suspended in 1N NaOH and re-exposed to ultrasound then filtered to give the title compound (0.077 g); mp 222°-224° C. (DMF-water-diethyl ether); δ (360 MHz, DMSO-d6) 2.17 (3H, s, CH3), 7.34-7.67 (8H, m, aromatics), 9.60 (1H, br s, NHSO2), 12.16 (1H, br s, NHCO); m/z (EI) 348 (M+).

Workup

  1. customThe solvent was removed in vacuo after one hour
  2. additiontreated with ultrasound for 5 mins
  3. filtrationbefore being filtered
  4. filtrationre-exposed to ultrasound then filtered

Sources & evidence

ORD record
ord-52f6326e2b2c4d51b8cdffe69215e731
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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