Dimethylformamide → HCID 86608946, compound

HRID 1985732Notes

Reaction equation

HRID 1985732 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][S:23][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:14](Br)[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.CN(C)[CH:51]=[O:52]>C1(C)C=CC=CC=1.CCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][S:23][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:14]([CH:51]=[O:52])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 69063830HCID 69063830, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86608946HCID 86608946, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8003PentaneSolvent

Procedure

To a solution of 0.39 g product of step 2 in 10 ml toluene was dropwise added 1.0 ml of a 1.7 M solution of tert-butyllithium in pentane at −78 C. The resulting orange solution was stirred at −78 C. for 15 min. to the resulting orange solution was added 1.00 ml dimethylformamide at −78 C. The initially read but soon bright yellow solution was stirred at −78 C. for 15 min and was then allowed to thaw to room temperature over 30 min. The reaction mixture was quenched with 10% aqueous ammonium chloride, the phases were separated and the organic phase was purified by chromatography on silica gel with dichloromethane:ethyl acetate=19:1. to yield 0.21 g of the title compound as colorless foam (MS: 606.4(M+H+)).

Workup

  1. stirringsoon bright yellow solution was stirred at −78 C
  2. customthaw to room temperature
  3. customover 30 min
  4. customThe reaction mixture was quenched with 10% aqueous ammonium chloride
  5. customthe phases were separated
  6. customthe organic phase was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-09703a706aa744f49efe78df55534ab0
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

Loading…