Trifluoroacetic acid → HCID 59002861, compound

HRID 561124Notes

Reaction equation

HRID 561124 reaction equation
[F:1][C:2]1[C:3]([NH:35][CH2:36][CH2:37][NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)=[C:4]2[O:9][CH2:8][C@@H:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:6]3[CH:16]=[C:17]([C:32]([OH:34])=[O:33])[C:18](=[O:31])[C:19]([C:20]=1[NH:21]CC1C=CC(OC)=CC=1)=[C:5]23.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:21][C:20]1[C:19]2[C:18](=[O:31])[C:17]([C:32]([OH:34])=[O:33])=[CH:16][N:6]3[C@H:7]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH2:8][O:9][C:4]([C:5]=23)=[C:3]([NH:35][CH2:36][CH2:37][NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:2]=1[F:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59002991HCID 59002991, compound

Product 1

HCID 59002861HCID 59002861, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-9-fluoro-2,3-dihydro-8-(4-methoxybenzylamino)-7-oxo-3-phenyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (366 mg, 0.614 mmol) in CH2Cl2 (10 mL) was added TFA (2.0 mL, 26.9 mmol) at 0° C. and the mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo. The solution of the residue in DMSO (3 mL) was added water and 2M aq. NaOH to adjust pH=7. A precipitate formed and was collected by filtration. The cake was added EtOH (10 mL), and boiled on water-bath. A precipitate was collected by and then dried to give (R)-8-amino-9-fluoro-2,3-dihydro-7-oxo-3-phenyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (124 mg, 42%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe solution of the residue in DMSO (3 mL) was added water and 2M aq. NaOH
  3. customA precipitate formed
  4. filtrationwas collected by filtration
  5. additionThe cake was added EtOH (10 mL)
  6. customboiled on water-bath
  7. customA precipitate was collected by and
  8. customthen dried

Sources & evidence

ORD record
ord-5b4b3bedda2d485fb4877b5445a9ce88
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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