Pyridine → HCID 67482641, compound

HRID 1191704Notes

Reaction equation

HRID 1191704 reaction equation
COC(=O)C1C=C[C:7]([NH:10][C:11](=[O:31])[CH2:12][S:13][CH:14]2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16](=[O:21])[N:15]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:6][CH:5]=1.C(Cl)(=O)C(Cl)=[O:35].CNC(N)=O.N1C=CC=CC=1>ClC1C=CC=CC=1.CN(C=O)C>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:15]2[C:16](=[O:21])[C:17]([CH3:20])=[C:18]([CH3:19])[CH:14]2[S:13][CH2:12][C:11]([NH:10][C:7]([NH:6][CH3:5])=[O:35])=[O:31])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 11719MethylureaHCID 65578Oxalyl chlorideHCID 16058694HCID 16058694, compound

Product 1

HCID 67482641HCID 67482641, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

The product from Example 1, Part C (200 mg, 0.6 mmol) was dissolved in 3 mL chlorobenzene and 2 drops DMF, then cooled to 0° C. Oxalyl chloride (0.72 mL, 2 M in CH2Cl2) was added and the mixture was stirred for 1 h while the temperature rose to room temperature. Methyl urea (133 mg, 1.2 mmol) was added and the mixture was stirred at 70° C. for 10 min. pyridine (0.12 mL, 1.2 mmol) was added and the mixture was stirred at 70° C. for 0.5 h. The reaction solvent was evaporated and the product was purified by silica gel chromatography. Recrystallization from CH2Cl2/ether provided the title compound as a white solid (130 mg, 55%). 1H NMR (400 MHz, CDCl3) δ 9.98 (br s, 1H), 8.21 (br s, 1H), 7.20 (d, J=8 Hz, 2H), 6.83 (d, J=8 Hz, 2H), 50.8 (d, J=15 Hz, 1H), 4.57 (s, 1H), 4.14 (d, J=15 Hz, 1H), 3.77 (s, 3H), 2.89 (m, 5H), 1.95 (s, 3H), 1.84 (s, 3H). MS: m/z (MH+) 378.

Workup

  1. customrose to room temperature
  2. additionwas added
  3. stirringthe mixture was stirred at 70° C. for 0.5 h
  4. customThe reaction solvent was evaporated
  5. customthe product was purified by silica gel chromatography
  6. customRecrystallization from CH2Cl2/ether

Sources & evidence

ORD record
ord-a2f271a1126a49c39586afb09e34fda8
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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