Benzenesulfonic Acid → 670220-93-6

HRID 351309Notes

Reaction equation

HRID 351309 reaction equation
[CH3:1][C:2]1([CH2:6][O:7][C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:15]4[CH:24]=[CH:23][C:22]5[C:17](=[C:18]([N:25]6[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]6)[CH:19]=[CH:20][CH:21]=5)[N:16]=4)[CH:13]=[N:14][C:10]=3[CH:9]=2)[CH2:5][O:4][CH2:3]1.[C:34]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)C>[C:34]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH3:1][C:2]1([CH2:6][O:7][C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:15]4[CH:24]=[CH:23][C:22]5[C:17](=[C:18]([N:25]6[CH2:26][CH2:27][CH:28]([NH2:31])[CH2:29][CH2:30]6)[CH:19]=[CH:20][CH:21]=5)[N:16]=4)[CH:13]=[N:14][C:10]=3[CH:9]=2)[CH2:5][O:4][CH2:3]1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 10366136Crenolanib

Product 1

HCID 18435899670220-93-6Yield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The compound, 1-{2-[5-(3-Methyl-oxetan-3-ylmethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine (2.44 9, 5.5 mmol, 1 equivalent) and ethanol (24 mL, 10 volumes) were added to a 100 mL round bottom flask. The solution was heated to reflux to dissolve the starting material and then cooled to room temperature. A solution of benzenesulfonic acid (918 mg, 5.2 mmol, 0.95 equivalents) in ethanol (5 mL, 2 volumes) was charged and the reaction was heated to reflux for ˜30 minutes. The reaction was cooled to 20–30° C. and allowed to granulate for 16–32 hours. The material was then filtered and dried under vacuum with a slight nitrogen bleed to afford 1-{2-[5-(3-Methyl-oxetan-3-ylmethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine benzenesulfonate (2.8 g, 85% yield) as an off-white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. dissolutionto dissolve the starting material
  4. temperaturethe reaction was heated
  5. temperatureto reflux for ˜30 minutes
  6. temperatureThe reaction was cooled to 20–30° C.
  7. waitto granulate for 16–32 hours
  8. filtrationThe material was then filtered
  9. customdried under vacuum with a slight nitrogen

Sources & evidence

ORD record
ord-bbb3abcd4f6644ca87d9d749e729bd4a
Source dataset
uspto-grants-2007_02
Patent number
US07183414B2

Reaction notes

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