4-Methoxybenzylamine → HCID 59002991, compound

HRID 561123Notes

Reaction equation

HRID 561123 reaction equation
F[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:25][CH2:26][CH2:27][NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:3]=1[F:35].[CH3:36][O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH2:43])=[CH:40][CH:39]=1>CS(C)=O>[F:35][C:3]1[C:4]([NH:25][CH2:26][CH2:27][NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[C:5]2[O:10][CH2:9][C@@H:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:7]3[CH:17]=[C:18]([C:22]([OH:24])=[O:23])[C:19](=[O:21])[C:20]([C:2]=1[NH:43][CH2:42][C:41]1[CH:44]=[CH:45][C:38]([O:37][CH3:36])=[CH:39][CH:40]=1)=[C:6]23

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 59003030HCID 59003030, compound

Product 1

HCID 59002991HCID 59002991, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (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 (432 mg, 0.903 mmol) and 4-methoxybenzylamine (400 μL, 4.51 mmol) in DMSO (4 mL) was stirred at 150° C. for 2 h. The reaction mixture was added portionwise at 0° C. with ice-water and the resulting precipitate was combined by filtration, washed with water. The cake washed with EtOH and collected by filtration and then dried to give (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 (411 mg, 78%) as a pale yellow solid.

Workup

  1. filtrationthe resulting precipitate was combined by filtration
  2. washwashed with water
  3. washThe cake washed with EtOH
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-c7d0c37016a84932897a269ccd52316d
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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