Piperidine → HCID 76552567, compound

HRID 2261141Notes

Reaction equation

HRID 2261141 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:10]=[CH:11][C:12]3[O:16][CH:15]=[C:14]([CH:17]=[CH:18][C:19]([OH:21])=O)[C:13]=3[CH:22]=2)[S:3]1.CCN(C(C)C)C(C)C.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C1COCC1>[O:21]=[C:19]([N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH:18]=[CH:17][C:14]1[C:13]2[CH:22]=[C:9]([CH:8]=[C:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])[CH:10]=[CH:11][C:12]=2[O:16][CH:15]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 73067167HCID 73067167, compound

Product 1

HCID 76552567HCID 76552567, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

180 mg (0.57 mmol) of 3-[5-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-benzofuran-3-yl]-acrylic acid (example 72) was suspended in THF (25 ml). To this suspension was added DIEA (2 eq.) and piperidine (3 eq.). Under stirring was added PyBOP (1.5 eq.). After 30 min the reaction mixture became clear, after an additional 1 h a precipitate was formed. The reaction was stirred overnight. The precipitate was filtered off and washed with THF and 1N HCl affording the title compound in high purity.

Workup

  1. customa precipitate was formed
  2. stirringThe reaction was stirred overnight
  3. filtrationThe precipitate was filtered off
  4. washwashed with THF and 1N HCl affording the title compound in high purity

Sources & evidence

ORD record
ord-ea18e84c9d6241beb835e4ec250025ff
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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