Methanol → HCID 68717464, compound

HRID 506394Notes

Reaction equation

HRID 506394 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]#N)[CH:27]=3)[C:22]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:44][CH3:45])=[O:5])[CH3:2].[OH-:46].[Na+].[CH3:48][OH:49]>>[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:33])[F:34])[CH:29]=[C:28]([C:36]([O:49][CH3:48])=[O:46])[CH:27]=3)[C:22]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:44][CH3:45])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68715690HCID 68715690, compound

Product 1

HCID 68717464HCID 68717464, compound

Procedure

(2R,4S)-4-{(3-Cyano-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 (315 mg) is dissolved in methanol (9 ml), and thereto is added 1N aqueous NaOH solution (1 ml). The mixture is stirred at room temperature for 1 day, and partitioned by adding 1N HCl and ethyl acetate. The organic layer is washed with saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=7:3→3:7→0:1) to give (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 (54 mg). MS (m/z): 659 [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 column chromatography (silica gel; hexane:ethyl acetate=7:3→3:7→0:1)

Sources & evidence

ORD record
ord-cb727567b06143b5992d2297fd4a707c
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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