Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 24936971, compound

HRID 561037Notes

Reaction equation

HRID 561037 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[F:18][C:19]1[C:20]([C:34]2[S:38][C:37]3[C:39]([C:43]4[C:48]([O:49][CH2:50][CH2:51][O:52]C5CCCCO5)=[CH:47][N:46]=[C:45]([F:59])[CH:44]=4)=[CH:40][CH:41]=[CH:42][C:36]=3[CH:35]=2)=[N:21][C:22]([NH:25][CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][NH:30][C:29]2=[O:33])=[N:23][CH:24]=1>C(O)C>[F:18][C:19]1[C:20]([C:34]2[S:38][C:37]3[C:39]([C:43]4[C:48]([O:49][CH2:50][CH2:51][OH:52])=[CH:47][N:46]=[C:45]([F:59])[CH:44]=4)=[CH:40][CH:41]=[CH:42][C:36]=3[CH:35]=2)=[N:21][C:22]([NH:25][CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][NH:30][C:29]2=[O:33])=[N:23][CH:24]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66998056HCID 66998056, compound

Product 1

HCID 24936971HCID 24936971, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Add pyridinium p-toluenesulfonate (4.3 mg, 0.02 mmol) to a solution of 1-{2-[5-fluoro-4-(7-{2-fluoro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-pyridin-4-yl}-benzo[b]thiophen-2-yl)-pyrimidin-2-ylamino]-ethyl}-imidazolidin-2-one (100 mg, 0.17 mmol) in ethanol (4 mL). Stir the mixture at 55° C. overnight. Cool the solution. Concentrate the solution in vacuo to yellow oil. Purify the oil by column chromatography (methylene chloride to 10% methanol in methylene chloride) to afford the title compound (75 mg, 87%) as a light yellow solid. MS (ES) m/z 513 [M+1]+.

Workup

  1. temperatureCool the solution
  2. concentrationConcentrate the solution in vacuo to yellow oil
  3. customPurify the oil by column chromatography (methylene chloride to 10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-b39ccc3ff9a04d92ad591860e9a83db8
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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