Hydrochloric Acid → Glesatinib

HRID 1475584Notes

Reaction equation

HRID 1475584 reaction equation
C(OC(=O)[N:7]([CH2:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][C:39](=[O:48])[CH2:40][C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)=[S:37])=[CH:31][C:30]=3[F:49])[CH:20]=2)=[CH:17][CH:18]=1)[CH2:8][CH2:9][O:10][CH3:11])(C)(C)C.Cl.O>CC(O)=O>[F:49][C:30]1[CH:31]=[C:32]([NH:35][C:36]([NH:38][C:39](=[O:48])[CH2:40][C:41]2[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=2)=[S:37])[CH:33]=[CH:34][C:29]=1[O:28][C:25]1[CH:24]=[CH:23][N:22]=[C:21]2[CH:20]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]([CH2:12][NH:7][CH2:8][CH2:9][O:10][CH3:11])=[CH:14][N:15]=3)[S:27][C:26]=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-7f8f9eda295a4d09ac488ba151adf908
Source dataset
uspto-grants-2015_04
Patent number
US09018378B2

Reaction notes

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