Water → HCID 86610569, compound

HRID 506342Notes

Reaction equation

HRID 506342 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]([F:39])([F:38])[F:37])[CH:27]=3)[C:22]([NH:40][C:41](=[O:46])[CH2:42][CH2:43][CH2:44]Cl)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:47][CH3:48])=[O:5])[CH3:2].[H-].[Na+].O>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:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:22]([N:40]3[CH2:44][CH2:43][CH2:42][C:41]3=[O:46])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:47][CH3:48])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86610570HCID 86610570, compound

Product 1

HCID 86610569HCID 86610569, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R*,4S*)-4-{[3,5-Bis(trifluoromethyl)benzyl]-[5-(4-chlorobutyrylamino)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (283 mg) is dissolved in N,N-dimethylformamide (4 ml), then thereto is added sodium hydride (18 mg) under ice-cooling, and the mixture is stirred at room temperature overnight. Water is added to the reaction solution and the mixture is extracted with ether. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=7:3→1:1) to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(2-oxopyrrolidin-1-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (132 mg). MS (m/z): 667 [M+H]+

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with ether
  3. washThe organic layer is washed with a 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→1:1)

Sources & evidence

ORD record
ord-c485c48a6bb0432283ef811c8e28f6ef
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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