Pyridine → HCID 178439852, compound

HRID 2407197Notes

Reaction equation

HRID 2407197 reaction equation
[CH2:1]([C:8]1[C:9]([NH:21][CH:22]([CH2:26][CH2:27][CH3:28])[C:23](O)=[O:24])=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:1]([C:8]1[NH:13][C:12]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[CH:11][N:10]2[C:23](=[O:24])[C:22]([CH2:26][CH2:27][CH3:28])=[N:21][C:9]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1363910332-((3-Benzyl-5-(4-hydroxyphenyl)pyrazin-2-yl)amino)pentanoic acid

Product 1

HCID 178439852HCID 178439852, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-((3-benzyl-5-(4-hydroxyphenyl)pyrazin-2-yl)amino)pentanoic acid (49 mg, 0.13 mmol) was dissolved in DCM (10 mL). Pyridine (0.5 mL) was added followed by N,N′-Dicyclohexylcarbodiimide (54 mg, 0.26 mmol). The reaction mixture was slowly stirred at room temperature for 1 hr. The solvent was evaporated, and the residue purified by flash chromatography (eluting solvent: EtOAc to DCM to 10% methanol in DCM) to give the product as a yellow powder (40 mg, 86%). NMR (300 MHz, CD3OD, δ): 7.35 (m, 8H), 6.88 (d, J=9.0 Hz, 2H), 4.40 (s, 2H), 2.81 (t, J=7.5 Hz, 2H), 1.81 (m, 2H), 1.02 (t, J=7.5 Hz, 3H); MS (ESI) m/z 359.0.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by flash chromatography (eluting solvent: EtOAc to DCM to 10% methanol in DCM)

Sources & evidence

ORD record
ord-14a77ac59040459cbbc6d1bcd1d5e256
Source dataset
uspto-grants-2014_08
Patent number
US08809529B2

Reaction notes

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