Hydrochloric Acid → HCID 59003030, compound

HRID 561122Notes

Reaction equation

HRID 561122 reaction equation
[F:1][C:2]1[C:20]2[C:19](=[O:21])[C:18]([C:22]([O:24]CC)=[O:23])=[CH:17][N:7]3[C@H:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:9][O:10][C:5]([C:6]=23)=[C:4]([NH:27][CH2:28][CH2:29][NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[C:3]=1[F:37].[OH-].[Na+].Cl.O>CCO>[F:1][C:2]1[C:20]2[C:19](=[O:21])[C:18]([C:22]([OH:24])=[O:23])=[CH:17][N:7]3[C@H:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:9][O:10][C:5]([C:6]=23)=[C:4]([NH:27][CH2:28][CH2:29][NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[C:3]=1[F:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59002885HCID 59002885, compound

Product 1

HCID 59003030HCID 59003030, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of ethyl (R)-8,9-difluoro-2,3-dihydro-7-oxo-3-phenyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate (627 mg, 1.24 mmol) in EtOH (8 mL) was added 2M aq. NaOH (6.20 mL, 12.4 mmol) at room temperature and the mixture was heated at 50° C. for 3 h. The reaction mixture was added 2N HCl (11.4 mL) and water. A precipitate formed and was collected by filtration, washed successively with water and then dried to give (R)-8,9-difluoro-2,3-dihydro-7-oxo-3-phenyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (452 mg, 75%) as a yellow solid.

Workup

  1. customA precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed successively with water
  4. customdried

Sources & evidence

ORD record
ord-e830c22a518144a0a00a2d06897827f1
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

Loading…