Pyridine → HCID 24961712, compound

HRID 1694649Notes

Reaction equation

HRID 1694649 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]4[CH:22]=[C:23]([CH:30]=[CH:31][CH:32]=4)[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])=[CH:14][CH:15]=3)[O:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]4[CH:22]=[C:23]([CH:30]=[CH:31][CH:32]=4)[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])=[CH:14][CH:15]=3)[O:10][CH:9]=2)=[CH:6][CH:7]=1)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 24962078HCID 24962078, compound

Product 1

HCID 24961712HCID 24961712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of prop-2-enyl 3-{[3-(4-aminophenyl)-4-oxochromen-7-yloxy]methyl}benzoate, prepared as described in Example 7A, (169.5 mg, 0.397 mmol) and anhydrous pyridine (34.5 mg, 0.44 mmol) in dry methylene chloride (3 ml) at 0° C. was added methanesulfonyl chloride (68.1 mg, 0.60 mmol). The mixture was then stirred at room temperature for 21 hours, then mixed with silics gel and the solvent removed under reduced pressure. Flash chromatography of the silica gel mixture, eluting with methylene chloride/methanol (99.5/0.5) gave prop-2-enyl 3-[(3-{4-[(methylsulfonyl)amino]phenyl}-4-oxochromen-7-yloxy)methyl]benzoate as a white solid (160.9 mg). (ESI) m/z 506 (M+H)+.

Workup

  1. customprepared
  2. additionmixed with silics gel
  3. customthe solvent removed under reduced pressure
  4. washFlash chromatography of the silica gel mixture, eluting with methylene chloride/methanol (99.5/0.5)

Sources & evidence

ORD record
ord-0704a772ec424189a055a50348d46d48
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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