Triethylamine → HCID 86601907, compound

HRID 478648Notes

Reaction equation

HRID 478648 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1(N)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].Cl.[CH:15]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)([CH3:17])[CH3:16].C1C=CC2N(O)N=[N:39]C=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:1]([CH2:3][NH:4][C:5]([C:7]1([C:31]2[CH:32]=[C:24]([CH:21]3[CH2:22][CH2:23][N:18]([CH:15]([CH3:17])[CH3:16])[CH2:19][CH2:20]3)[CH:25]=[CH:26][C:27]=2[C:28]([NH2:39])=[O:29])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amideHCID 69129801HCID 69129801, compound

Product 1

HCID 86601907HCID 86601907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Amino-cyclohexanecarboxylic acid cyanomethyl-amide (0.95 mmol), 4-(1-isopropyl-piperidin-4-yl)-benzoic acid hydrochloride (0.95 mmol), HOBT (0.95 mmol), WSCD (0.95 mmol) and triethylamine (0.95 mmol) are dissolved in DMF (5 ml) and stirred overnight at rt. After evaporation of the solvent, the residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions) and extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A white powder with mp. 214-216° C., Rf=0.38 (CH2Cl2/MeOH (with 3N NH3)=9:1) is obtained.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions)
  3. extractionextracted three times with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialis dried over sodium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA white powder with mp. 214-216° C., Rf=0.38 (CH2Cl2/MeOH (with 3N NH3)=9:1) is obtained

Sources & evidence

ORD record
ord-4ffc217dedc945af8278fd3e2cbddcc7
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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