2,3-Dihydroxybutanedioic Acid → HCID 178424608, compound

HRID 232022Notes

Reaction equation

HRID 232022 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[N:10][N:11]([O:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS[C:20]1[NH:21][CH:22]=[C:23]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[N:32][CH:33]=2)[C:24](=[O:26])[N:25]=1.C(O)(=O)C(C(C(O)=O)O)O>N1C=CC=CC=1.C(O)(C)C>[N:1]1([CH2:7][C:8]2[CH:9]=[N:10][N:11]([O:13][CH2:14][CH2:15][CH2:16][NH:17][C:20]3[NH:21][CH:22]=[C:23]([CH2:27][C:28]4[CH:29]=[CH:30][C:31]([CH3:34])=[N:32][CH:33]=4)[C:24](=[O:26])[N:25]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 138232143-(4-Piperidinomethylpyrazol-1-yloxy)propylamineHCID 178503537HCID 178503537, compound

Product 1

HCID 178424608HCID 178424608, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3776IsopropanolSolvent

Procedure

3.5 g of 3-(4-piperidinomethylpyrazol-1-yloxy)propylamine and 3.6 g of 2-methylthio-5-(2-methylpyrid-5-ylmethyl)-1H-pyrimid-4-one in 30 ml of pyridine are refluxed for 30 hours. The pyridine is distilled off and the residue is then chromatographed over neutral Al2O3 (activity level III) using methylene chloride/3% strength methanol as the mobile phase. The oil obtained is reacted with tartaric acid in isopropanol to give an amorphous solid.

Workup

  1. distillationThe pyridine is distilled off
  2. customthe residue is then chromatographed over neutral Al2O3 (activity level III)
  3. customThe oil obtained
  4. customto give an amorphous solid

Sources & evidence

ORD record
ord-e8522393088a431c8f6a3da6b41f6ee4
Source dataset
uspto-grants-1989_07
Patent number
US04851410

Reaction notes

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