Succinic anhydride → N-(5-Chloro-2-{2-[4-(4-Fluoro-Benzyl)-(2R)-2-Methyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Pyridin-3-yl)-Succinamic Acid

HRID 11675Notes

Reaction equation

HRID 11675 reaction equation
[NH2:1][C:2]1[C:3]([O:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:15][C@H:14]2[CH3:27])=[O:12])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.CN1CCOCC1.[C:35]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36]1>ClCCl>[Cl:8][C:6]1[CH:7]=[C:2]([NH:1][C:35](=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=[O:39])[C:3]([O:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:15][C@H:14]2[CH3:27])=[O:12])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 79724-MethylmorpholineHCID 696554982-(3-Amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

Product 1

HCID 69655375N-(5-Chloro-2-{2-[4-(4-Fluoro-Benzyl)-(2R)-2-Methyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Pyridin-3-yl)-Succinamic AcidYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3-amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.10 g, 0.26 mmol) in dichloromethane (3 mL) was added N-methylmorpholine (0.028 mL, 0.26 mmol) and succinic anhydride (0.026 g, 0.26 mmol). The reaction was stirred at ambient temperature for 3 days. The reaction was diluted with dichlormethane and washed with 1N hydrochloric acid solution. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.040 g, LRMS: 493.2).

Workup

  1. washwashed with 1N hydrochloric acid solution
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af3ddef924814e8aae1e9435c057a29f
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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