Sodium Carbonate → HCID 87279408, compound

HRID 2273794Notes

Reaction equation

HRID 2273794 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:27][C:28]#[N:29]>CN(C)C=O>[C:28]([CH2:27][N:13]1[CH2:14][CH2:15][C@@H:11]([NH:10][C:9]2[CH:8]=[CH:7][C:6]([S:16]([NH2:19])(=[O:17])=[O:18])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:12]1)#[N:29]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11534BromoacetonitrileHCID 67126429HCID 67126429, compound

Product 1

HCID 87279408HCID 87279408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of EXAMPLE 428C (440 mg) in anhydrous N,N-dimethylformamide (10 mL) was added sodium carbonate (132 mg). To the resulting suspension was added 2-bromoacetonitrile (0.077 mL) and the mixture was heated at 60° C. for 18 hours. The crude material was isolated by concentration and was purified on silica gel, and was eluted with a 0.5, 2.5, and 5% methanol in methylene chloride step gradient to provide the title compound.

Workup

  1. customThe crude material was isolated by concentration
  2. customwas purified on silica gel
  3. washwas eluted with a 0.5, 2.5, and 5% methanol in methylene chloride step gradient

Sources & evidence

ORD record
ord-f8c081941d3543f488ba7e7b5891c658
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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