HCID 11634332, compound → HCID 11591022, compound

HRID 418993Notes

Reaction equation

HRID 418993 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([CH:19]([OH:26])[C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[O:26])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:27]([F:30])([F:28])[F:29]

Participants

3

Reactant 2

HCID 11634332HCID 11634332, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11591022HCID 11591022, compound

Procedure

A mixture of 4-chloro-N-[5-chloro-2-(hydroxy-pyridin-4-yl-methyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (15 mg, 0.03 mmol) and PCC (15 mg) was stirred at room temperature for 2 h. It was then treated with small amount of silica gel and filtered. The filtrate was concentrated under reduced pressure to provide the crude ketone. 1H NMR (400 MHz, CDCl3) δ 10.90 (br s, 1 H), 8.78 (dd, J=4.4, 1.6 Hz, 2 H), 8.35 (d, J=2.0 Hz, 1 H), 8.19-8.17 (m, 2 H), 7.98 (dd, J=8.4, 2.0 Hz, 1 H), 7.65-7.61 (m, 3 H). MS m/z: 476.0 (M+H).

Workup

  1. additionIt was then treated with small amount of silica gel
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c1e192252a3e47aaa41411f8d96c3182
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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