Dimethylamine → HCID 42606695, compound

HRID 2092934Notes

Reaction equation

HRID 2092934 reaction equation
[Br:1][C:2]1[C:3]([CH2:20][C:21]([NH:23][N:24]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:25]2[C:30]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:37])=[O:22])=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:17]=1)[C:7]([O:9]N1C(=O)CCC1=O)=O.[CH3:46][NH:47][CH3:48]>C1COCC1>[Br:1][C:2]1[C:3]([CH2:20][C:21]([NH:23][N:24]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:25]2[C:30]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:37])=[O:22])=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:17]=1)[C:7]([N:47]([CH3:48])[CH3:46])=[O:9]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86647346HCID 86647346, compound

Product 1

HCID 42606695HCID 42606695, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 85 mg of the compound obtained in stage 8 of Example 1 in 500 μL of THF are added at room temperature 2 mL (29 equivalents) of a 2 M dimethylamine solution in THF. The reaction medium is then stirred for 2 hours before being dry evaporated. The obtained white solid is taken up in 10 mL of ethyl acetate. The resulting organic phase is washed several times with water and then with a saturated NaCl solution, dried on sodium sulphate, dry evaporated. The raw product is chromatographed on silica gel (dichloromethane/methanol:98/2) in order to provide 45 mg of the expected compound as a white solid.

Workup

  1. custombefore being dry
  2. customevaporated
  3. washThe resulting organic phase is washed several times with water
  4. dry with materialwith a saturated NaCl solution, dried on sodium sulphate
  5. customdry
  6. customevaporated
  7. customThe raw product is chromatographed on silica gel (dichloromethane/methanol:98/2) in order

Sources & evidence

ORD record
ord-a78b5fb3289a42c78ad87afab1967523
Source dataset
uspto-grants-2013_05
Patent number
US08440833B2

Reaction notes

Loading…