HCID 57967263, compound → Glesatinib

HRID 1475580Notes

Reaction equation

HRID 1475580 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>C(O)(C(F)(F)F)=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

3

Reactant 1

HCID 57967263HCID 57967263, compound

Product 1

HCID 25181472GlesatinibYield 63%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To solid 14 (7.00 g, 9.72 mmol) in a 250 mL round-bottom flask was added TFA (20 mL). The addition was a little bit exothermic. The mixture was stirred at r.t. for 2 h then concentrated and co-evaporated with MTBE (2×100 mL) to obtain a solid that was triturated with MTBE (80 mL) for 2 h. The solid was collected by filtration, washed with MTBE (2×10 mL) and dried in vacuum for 1 h. The dry solid was partitioned between the mixture of DCM/MeOH: (9/1, 300 mL) and NaHCO3 (200 mL). The phases were separated. The organic phase was collected and the aqueous phase was extracted with DCM/MeOH: 9/1 (2×150 mL). Organic phases were combined, washed with brine (100 mL), dried over Na2SO4 and concentrated. The solid residue was triturated with EA (40 mL) for 1 h, collected by filtration, washed with EA (2×5 mL), dried in vacuum for 1 h to afford 15 as beige solid (3.77 g, 63% yield). MS (m/z): 620.6 (M+1).

Workup

  1. additionThe addition
  2. concentrationthen concentrated
  3. customto obtain a solid
  4. customthat was triturated with MTBE (80 mL) for 2 h
  5. filtrationThe solid was collected by filtration
  6. washwashed with MTBE (2×10 mL)
  7. customdried in vacuum for 1 h
  8. customThe dry solid was partitioned between the mixture of DCM/MeOH
  9. customThe phases were separated
  10. customThe organic phase was collected
  11. extractionthe aqueous phase was extracted with DCM/MeOH
  12. washwashed with brine (100 mL)
  13. dry with materialdried over Na2SO4
  14. concentrationconcentrated
  15. customThe solid residue was triturated with EA (40 mL) for 1 h
  16. filtrationcollected by filtration
  17. washwashed with EA (2×5 mL)
  18. customdried in vacuum for 1 h

Sources & evidence

ORD record
ord-83f44757274b4535ab327d648cb83bb8
Source dataset
uspto-grants-2015_04
Patent number
US09018378B2

Reaction notes

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