Trifluoroacetic acid → HCID 59002962, compound

HRID 561144Notes

Reaction equation

HRID 561144 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH:26]CC4C=CC(OC)=CC=4)[C:10]([F:25])=[C:11]([NH:15][CH2:16][CH2:17][NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[C:12]=3[F:14])[C:7](=[O:36])[CH:6]=[C:5]2[C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:26][C:9]1[C:10]([F:25])=[C:11]([NH:15][CH2:16][CH2:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:12]([F:14])=[C:13]2[C:8]=1[C:7](=[O:36])[CH:6]=[C:5]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:4]2[CH:1]1[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59002902HCID 59002902, compound

Product 1

HCID 59002962HCID 59002962, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 1-cyclopropyl-6,8-difluoro-1,4-dihydro-5-(4-methoxybenzylamino)-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-2-carboxylate (577 mg, 1.02 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. and treated dropwise with trifluoroacetic acid (2 mL). The reaction mixture was stirred at room temperature for over night. The reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3, brine, and dried over anhyd Na2SO4 followed by the removal of CH2Cl2. The crude product was purified by column chromatography (Hexane:EtOAc 1:1) to yield ethyl 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-2-carboxylate (336 mg, 74%) as a orange amorphous solid.

Workup

  1. washwashed with saturated NaHCO3, brine
  2. dry with materialdried over anhyd Na2SO4
  3. customfollowed by the removal of CH2Cl2
  4. customThe crude product was purified by column chromatography (Hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-49ff6b540c734a66bc30f00ff785b2fb
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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