Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 44217942, compound

HRID 1928738Notes

Reaction equation

HRID 1928738 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:22]([N:24]4[CH2:29][CH2:28][CH:27]([CH2:30][O:31]C5CCCCO5)[CH2:26][CH2:25]4)=[O:23])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO.O>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:22]([N:24]4[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]4)=[O:23])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86634164HCID 86634164, compound

Product 1

HCID 44217942HCID 44217942, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

4-(Tetrahydro-pyran-2-yloxymethyl)-piperidine-1-carboxylic acid [2-((R)-indan-1-ylamino)-quinolin-6-yl]-amide (0.070 g) was dissolved in methanol (1 mL). Pyridinium toluene-4-sulfonate (11.0 mg) was added and the reaction mixture stirred at 55° C. for 1 h. The reaction mixtures was diluted with water and extracted with ethyl acetate. The combined organic phases were dried on sodium sulfate, evaporated and the residue was subjected to column chromatography (silica gel, dichloro methane:methanol gradient=100:0→90:10) to yield the title compound (35 mg; 60%) as an off-white solid; MS: m/e=416.7 (M+H+).

Workup

  1. customThe reaction mixtures
  2. extractionextracted with ethyl acetate
  3. customThe combined organic phases were dried on sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c141d5e8b5414877a8884c0e6b8f6f85
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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