Cyclopropanecarboxylic acid → HCID 57635342, compound

HRID 535927Notes

Reaction equation

HRID 535927 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[C:29]1([C:35]2[N:39]3[CH2:40][CH2:41][NH:42][CH2:43][C:38]3=[C:37]([C:44]([NH:46][CH:47]3[C:52]([CH3:54])([CH3:53])[CH:51]4[CH2:55][C:48]3([CH3:56])[CH2:49][CH2:50]4)=[O:45])[N:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH:1]1([C:4]([N:42]2[CH2:41][CH2:40][N:39]3[C:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:36][C:37]([C:44]([NH:46][CH:47]4[C:52]([CH3:53])([CH3:54])[CH:51]5[CH2:55][C:48]4([CH3:56])[CH2:49][CH2:50]5)=[O:45])=[C:38]3[CH2:43]2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66931715HCID 66931715, compound

Product 1

HCID 57635342HCID 57635342, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclopropanecarboxylic acid (1.2 eq.) in anhydrous DMF (2 mL) was distributed EDCI (1.6 eq.), HOBt (1.3 eq.) and TEA (5 eq.). The vial was sealed and stirred for 40 minutes at room temperature. Compound 39 (1 eq. in 1 mL of anhydrous DMF) was added to the vial which was then sealed and stirred overnight at room temperature. The solvent was removed by centrifugal evaporation under reduced pressure. The residue was dissolved in DCM (2 mL), and washed sequentially with 10% K2CO3 solution (1 mL) and water (1 mL). The water wash was then re-extracted with DCM (0.5 mL), the combined organic extracts were evaporated to dryness under reduced pressure. The desired product, Compound 119, was isolated by mass directed LC. LCMS (+ESI) m/z 447.38 [M+H]+

Workup

  1. customThe vial was sealed
  2. customwas then sealed
  3. stirringstirred overnight at room temperature
  4. customThe solvent was removed by centrifugal evaporation under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (2 mL)
  6. washwashed sequentially with 10% K2CO3 solution (1 mL) and water (1 mL)
  7. washThe water wash
  8. extractionwas then re-extracted with DCM (0.5 mL)
  9. customthe combined organic extracts were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cb4ffa4340f143ab88a40eb0daea6c4b
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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