Ethyl bromoacetate → HCID 86610639, compound

HRID 506389Notes

Reaction equation

HRID 506389 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]([CH2:40][OH:41])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:42][CH3:43])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:51][C:52]([O:54]CC)=[O:53]>CC(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:27]=[C:28]([C:36]([F:37])([F:38])[F:39])[CH:29]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:31]=3)[C:22]([CH2:40][O:41][CH2:51][C:52]([OH:54])=[O:53])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:42][CH3:43])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 86610583HCID 86610583, compound

Product 1

HCID 86610639HCID 86610639, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(2R,4S)-4-{[3,5-Bis(trifluoromethyl)benzyl]-(5-hydroxymethyl-pyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (130 mg) is dissolved in acetone (2.5 ml), and thereto are added potassium carbonate (108 mg) and ethyl bromoacetate (0.129 ml). The mixture is stirred at room temperature for 6 days. The reaction solution is concentrated under reduced pressure, and thereto is added water. The mixture is stirred for 40 hours, and partitioned by adding chloroform to the reaction solution. The organic layer is dried over magnesium sulfate, then concentrated under reduced pressure to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-(5-carboxymethoxymethylpyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (33.8 mg). MS (m/z): 672 [M+H]+.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionis added water
  3. stirringThe mixture is stirred for 40 hours
  4. custompartitioned
  5. additionby adding chloroform to the reaction solution
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4158c643ae224d7a813f83340aaccab1
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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