Dimethylformamide → HCID 16737152, compound

HRID 254262Notes

Reaction equation

HRID 254262 reaction equation
[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][CH2:9][N:10]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:11](=[O:22])[NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].I[CH:49]([CH3:51])[CH3:50]>CC(C)=O>[CH:49]([O:17][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([NH:12][C:11]([N:10]([CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:22])[CH:14]=1)([CH3:51])[CH3:50]

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 16737307HCID 16737307, compound

Product 1

HCID 16737152HCID 16737152, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

200 mg (0.41 mmol, 1 eq.) of product of Example 45 are dissolved in 2 mL of acetone and 2 mL of dry DMF under argon. 283 mg (2.05 mmol, 5 eq.) of K2CO3 and 328 μL (3.28 mmol, 8 eq.) of 2-iodopropane, the mixture is heated under reflux for 2 hours. The medium is then concentrated and taken up in water and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water then brine, dried over MgSO4, filtered and concentrated. The oil obtained is freed from DMF by entraining the DMF to the rotary evaporator with ethyl acetate, then dried with a vane pump. The product is obtained in the form of white crystals (m=214 mg, yield=99%).

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe medium is then concentrated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oil obtained
  9. customto the rotary evaporator with ethyl acetate
  10. customdried with a vane pump
  11. customThe product is obtained in the form of white crystals (m=214 mg, yield=99%)

Sources & evidence

ORD record
ord-142a108d129b48cea88c159a24569277
Source dataset
uspto-grants-2011_01
Patent number
US07875609B2

Reaction notes

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