Hydrochloric Acid → Glesatinib

HRID 1401356Notes

Reaction equation

HRID 1401356 reaction equation
[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([NH:40][C:41](=[O:50])[CH2:42][C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)=[S:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH3:32])C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)[S:13][C:6]=12.Cl.O>CC(O)=O>[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([NH:40][C:41](=[O:50])[CH2:42][C:43]2[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=2)=[S:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][NH:21][CH2:29][CH2:30][O:31][CH3:32])=[CH:18][N:19]=3)[S:13][C:6]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 57967263HCID 57967263, compound

Product 1

HCID 25181472Glesatinib

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 14 (45.06 g, 62.6 mmol, 1 eq.,) in AcOH (338 mL) was added 1N HCl (188 mL) over 1 min. The reaction mixture was heated at 40° C. for 2 h. After cooling down to r.t., water (676 mL) was added. The reaction mixture turned into a suspension and was stirred at r.t. for 15 min. The solid was collected by filtration and the product cake was washed with water (2×100 mL) then dried in vacuum for 30 min to afford a crude hydrochloride salt of 15 as a white solid.

Workup

  1. temperatureAfter cooling down to r.t.
  2. filtrationThe solid was collected by filtration
  3. washthe product cake was washed with water (2×100 mL)
  4. customthen dried in vacuum for 30 min

Sources & evidence

ORD record
ord-671f8074ff3b4169be5152e578ca89fe
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

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