HCID 57967263, compound → Glesatinib

HRID 1401352Notes

Reaction equation

HRID 1401352 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>C(O)(C(F)(F)F)=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

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-91d08539e5c94d71944d4d278f4257de
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

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