Water → HCID 58097243, compound

HRID 1913490Notes

Reaction equation

HRID 1913490 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:12][CH:11]=2)[C:5]([C:27]#[N:28])=[C:4]([S:29][CH2:30][C:31]2[N:32]=[C:33]([C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)[S:34][CH:35]=2)[N:3]=1.[H-].[Na+].Br[CH2:46][C:47]([O:49][CH3:50])=[O:48].[OH2:51]>CN(C=O)C>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][C:4]([S:29][CH2:30][C:31]3[N:32]=[C:33]([C:36]4[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=4)[S:34][CH:35]=3)=[C:5]([C:27]#[N:28])[C:6]=2[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21])=[CH:12][CH:11]=2)[N:1]([CH2:46][C:47]([O:49][CH3:50])=[O:48])[C:12]=1[C:13]([O:16][CH3:17])=[O:51]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 66671817HCID 66671817, compound

Product 1

HCID 58097243HCID 58097243, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under argon, 230 mg (0.363 mmol) of the compound from Example 32A were initially charged in 4 ml of DMF, 17 mg (60% pure, 0.435 mmol) of sodium hydride were added a little at a time and the mixture was then stirred at RT for 30 min. A solution of 41 μl (0.435 mmol) of methyl bromoacetate in 1 ml of DMF was then added dropwise, and the resulting solution was stirred at RT overnight. Water was added, and the reaction mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

  1. stirringthe resulting solution was stirred at RT overnight
  2. extractionthe reaction mixture was extracted three times with ethyl acetate
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record
ord-fceab37b0b1f4eec8f9ea6d07f32747b
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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