Trifluoroacetic acid → HCID 10296729, compound

HRID 2180126Notes

Reaction equation

HRID 2180126 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([O:26][C:27]4[C:28]([F:37])=[C:29]5[C:33](=[CH:34][CH:35]=4)[NH:32][C:31]([CH3:36])=[CH:30]5)=[CH:21][N:22]=[N:23]3)=[CH:18][C:17]=2[O:38][CH3:39])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:37][C:28]1[C:27]([O:26][C:20]2[C:19]3[C:24](=[CH:25][C:16]([O:15][CH2:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[C:17]([O:38][CH3:39])[CH:18]=3)[N:23]=[N:22][CH:21]=2)=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]=[C:31]([CH3:36])[NH:32]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22490023HCID 22490023, compound

Product 1

HCID 10296729HCID 10296729, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxycinnoline (100 mg, 0.186 mmol) in methylene chloride (3 ml) containing TFA (1 ml) was stirred at ambient temperature for 2 hours. The volatiles were removed under vacuum. The residue was partitioned between water and methylene chloride and the pH of the aqueous layer was adjusted to 13 with 6N aqueous sodium hydroxide. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was triturated with ether/pentane (1/1). The solid was filtered, washed with pentane and dried under vacuum to give 4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(piperidin-4-ylmethoxy)cinnoline (50 mg, 62%).

Workup

  1. customThe volatiles were removed under vacuum
  2. customThe residue was partitioned between water and methylene chloride
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with ether/pentane (1/1)
  8. filtrationThe solid was filtered
  9. washwashed with pentane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-6512357a607b41b3a80792141612a370
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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