Dicyclohexylcarbodiimide → HCID 86691596, compound

HRID 333948

Reaction equation

HRID 333948 reaction equation
[OH:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C1CCC(N=C=NC2CCCCC2)CC1.C1C=NC2N(O)N=NC=2C=1.[CH3:34][C:35]1[CH:44]=[C:43]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=1>CN(C=O)C>[OH:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([N:48]1[CH2:49][CH2:50][N:45]([C:43]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]=[C:35]([CH3:34])[CH:44]=2)[CH2:46][CH2:47]1)=[O:7]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 7023182-Methyl-4-(piperazin-1-yl)quinolineHCID 53636584-Hydroxy-pent-2-enoic acid

Product 1

HCID 86691596HCID 86691596, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-4-Hydroxypent-2-enoic acid (67 mg, 0.52 mmol) was dissolved in anhydrous DMF (2.5 ml), DCC (107.5, 0.52 mmol) and HOAt (106.7 mg, 0.79 mmol) were added and the mixture was stirred at room temperature for 15 minutes. 2-Methyl-4-piperazin-1-yl-quinoline (118.2 mg, 0.52 mmol) was added and stirring was continued for 90 minutes. The mixture was evaporated to dryness, taken up in a mixture of acetonitrile and methanol and filtered. The filtrate was evaporated to dryness again and purified by preparative HPLC (gradient of water containing 0.1% TFA and acetonitrile). 110 mg were obtained (0.33 mmol, 65%). MS (ES): m/z=326.1 [M+1]+.

Workup

  1. stirringstirring
  2. waitwas continued for 90 minutes
  3. customThe mixture was evaporated to dryness
  4. additiontaken up in a mixture of acetonitrile and methanol
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness again
  7. custompurified by preparative HPLC (gradient of water containing 0.1% TFA and acetonitrile)
  8. custom110 mg were obtained (0.33 mmol, 65%)

Sources & evidence

ORD record
ord-f702141a66674518bc41b725648f1e79
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

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