Trifluoroacetic acid → HCID 59002911, compound

HRID 561127Notes

Reaction equation

HRID 561127 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 59002955HCID 59002955, compound

Product 1

HCID 59002911HCID 59002911, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-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 (355 mg, 0.596 mmol) in CH2Cl2 (4 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 was added to adjust pH=7. A precipitate formed and was collected by filtration. The cake was added to EtOH (10 mL), and boiled on water-bath. A precipitate was collected by and then dried to give (S)-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 (163 mg, 58%) 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. additionwas added
  4. customA precipitate formed
  5. filtrationwas collected by filtration
  6. additionThe cake was added to EtOH (10 mL)
  7. customboiled on water-bath
  8. customA precipitate was collected by and
  9. customthen dried

Sources & evidence

ORD record
ord-cf4878dc78404f26a52f821a881f807f
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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