Water → HCID 58659338, compound

HRID 1993532Notes

Reaction equation

HRID 1993532 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[O:18])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C(Cl)Cl.O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[O:2]=[C:3]1[NH:8][CH:7]=[C:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[O:18])=[CH:14][CH:15]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 58659428HCID 58659428, compound

Product 1

HCID 58659338HCID 58659338, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-(4-(6-methoxy-pyridin-3-ylmethyl)-phenyl)-N′-(4-methyl-phenyl)-urea (Example 95; 0.28 g, 0.81 mmol) and trimethylsilyl-jodide (0.6 ml) in chloroform (10 ml) is stirred for 16 h at 60° C. Then CH2Cl2 (4 ml), water (10 ml) and saturated NaHCO3 solution (5 ml) is added and the suspension stirred vigorously. Filtration, washing with CH2Cl2 and water followed by column chromatography (SiO2; AcOEt/MeOH 9:1→4:1 MeOH) yields the title compound: 1H-NMR (DMSO-d6): 11.4 (s, HN), 8.52 (s, HN), 8.47 (s, HN), 7.33 (d, 2H), 7.29 (d, 2H), 7.25 (dd, 1H), 7.16 (s, 1H), 7.07 (d, 2H), 7.04 (d, 2H), 6.24 (d, 1H), 3.58 (s, 2H), 2.22 (s, 3H).

Workup

  1. stirringthe suspension stirred vigorously
  2. filtrationFiltration
  3. washwashing with CH2Cl2 and water

Sources & evidence

ORD record
ord-5fc5b4cdc47f43cbbe800aaa2f3be04f
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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