Potassium Carbonate → HCID 86610627, compound

HRID 506383Notes

Reaction equation

HRID 506383 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][CH3:41])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:42][CH3:43])=[O:5])[CH3:2].Br[CH2:45][CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49].C(=O)([O-])[O-].[K+].[K+]>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:38])([F:39])[F:37])[CH:27]=3)[C:22]([NH:40][CH2:41][CH2:45][CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:42][CH3:43])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 86610625HCID 86610625, compound

Product 1

HCID 86610627HCID 86610627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

(2R,4S)-4-{[3,5-Bis(trifluoromethyl)benzyl]-(5-methylaminopyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (150 mg) is dissolved in N,N-dimethylformamide (5 ml), and thereto are added ethyl 4-bromobutyrate (13 μl) and potassium carbonate (50 mg). The mixture is heated at 50° C. and stirred for 2 hours. The reaction solution is cooled to room temperature, and partitioned by adding a saturated aqueous sodium hydrogen carbonate solution 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=9:1→3:2) to give (2R,4S)-4-([3,5-bis(trifluoromethyl)benzyl]-{5-[(3-ethoxycarbonylpropyl)-methyl]aminopyrimidin-2-yl})amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (85 mg). MS (m/z): 727 [M+H]+.

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. custompartitioned
  3. additionby adding a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  4. washThe organic layer is washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=9:1→3:2)

Sources & evidence

ORD record
ord-cf13841fe10541389a5a4061728ca7e5
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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