Cyclopropanecarboxylic acid → HCID 57635342, compound

HRID 2110196Notes

Reaction equation

HRID 2110196 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-70cc4942efc34691a5146186cc1100fd
Source dataset
uspto-grants-2009_04
Patent number
US07517874B2

Reaction notes

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