Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 25120910, compound

HRID 1640931Notes

Reaction equation

HRID 1640931 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:33]2[S:37][C:36]3[C:38]([C:42]4[C:47]([O:48][CH2:49][CH2:50][O:51]C5CCCCO5)=[CH:46][N:45]=[C:44]([F:58])[CH:43]=4)=[CH:39][CH:40]=[CH:41][C:35]=3[CH:34]=2)=[N:21][C:22]([NH:25][CH2:26][CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[N:29]2)=[N:23][CH:24]=1>C(O)C>[N:28]1([CH2:27][CH2:26][NH:25][C:22]2[N:21]=[C:20]([C:33]3[S:37][C:36]4[C:38]([C:42]5[CH:43]=[C:44]([F:58])[N:45]=[CH:46][C:47]=5[O:48][CH2:49][CH2:50][OH:51])=[CH:39][CH:40]=[CH:41][C:35]=4[CH:34]=3)[C:19]([F:18])=[CH:24][N:23]=2)[CH:32]=[CH:31][N:30]=[N:29]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66738550HCID 66738550, compound

Product 1

HCID 25120910HCID 25120910, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Add pyridinium p-toluenesulfonate (8.23 mg, 0.03 mmol) to a solution of [5-fluoro-4-(7-{2-fluoro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-pyridin-4-yl}-benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-(2-[1,2,3]triazol-1-yl-ethyl)-amine (190 mg, 0.32 mmol) in ethanol (4 mL). Stir the mixture at 55° C. overnight. Cool the solution. Concentrate the solution in vacuo to a yellow oil. Purify by column chromatography (methylene chloride to 10% methanol in methylene chloride) to afford the title compound (0.14 g, 88%) as a light yellow solid. MS (ES) m/z 496 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-418e8812162248f4846f3c8106804bc2
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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