p-Toluenesulfonic acid monohydrate → HCID 86624306, compound

HRID 578164Notes

Reaction equation

HRID 578164 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[N:18][CH:19]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].O.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(OCC)(=O)C>[S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)([OH:30])(=[O:29])=[O:28].[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[N:18][CH:19]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 44544775HCID 44544775, compound

Product 1

HCID 86624306HCID 86624306, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of the product of Example 101A (52 mg, 0.2 mmol) in ethyl acetate (5 mL) was stirred with a solution of p-toluenesulfonic acid monohydrate (Aldrich, 46.0 mg, 0.24 mmol) in ethyl acetate (1.0 mL) at ambient temperature for 10 hours. The precipitates were collected by filtration and dried to give the title compound. 1H NMR (300 MHz, CDCl3) δ 2.40 (s, 3H), 7.25 (d, J=8.2 Hz, 2H), 7.36-7.53 (m, 1H), 7.83 (d, J=8.3 Hz, 2H), 8.03-8.12 (m, 2H), 9.57 (s, 1H), 9.71 (s, 2H); MS (DCI/NH3) m/z 261 (M+H)+.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-b4b01a69ba184fbab541cbb951549e0a
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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