Sodium Hydroxide → HCID 68717324, compound

HRID 506395Notes

Reaction equation

HRID 506395 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[N:24]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([O:38]C)=[O:37])[CH:27]=3)[C:22]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:46][CH3:47])=[O:5])[CH3:2].[OH-].[Na+]>CO.CN(C)C=O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[N:24]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=[C:28]([C:36]([OH:38])=[O:37])[CH:27]=3)[C:22]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:46][CH3:47])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68717464HCID 68717464, compound

Product 1

HCID 68717324HCID 68717324, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

(2R,4S)-2-Ethyl-6-methoxy-4-{(3-methoxycarbonyl-5-trifluoromethylbenzyl)-[5-(morpholin-4-yl)pyrimidin-2-yl]}amino-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (86 mg) is dissolved in methanol (9 ml) and N,N-dimethylformamide (1 ml), and thereto is added 1N aqueous NaOH solution (3 ml). The mixture is stirred at room temperature for 1.5 hours, and partitioned by adding 1N HCl and ethyl acetate. The organic layer is washed with saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by thin layer silica gel chromatography (chloroform:methanol=9:1) to give (2R,4S)-4-{(3-carboxy-5-trifluoromethylbenzyl)-[5-(morpholin-4-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (25 mg). MS (m/z): 645 [M+H]+.

Workup

  1. custompartitioned
  2. additionby adding 1N HCl and ethyl acetate
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by thin layer silica gel chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-e64ee57bdf3842ba91b0eeb1230e356d
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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