Sodium Chloride → HCID 22136497, compound

HRID 1827261Notes

Reaction equation

HRID 1827261 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.O1CCOCC1.[Cl-].[Na+].[NH2:42][NH2:43]>>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:5]3[C:4](=[CH:9][CH:8]=[C:7]([C:19]([C:27]4[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=4)([C:21]4[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=4)[OH:20])[CH:6]=3)[N:3]=[C:2]([NH:42][NH2:43])[N:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 9321HydrazineHCID 312751,4-DioxaneHCID 22136471HCID 22136471, compound

Product 1

HCID 22136497HCID 22136497, compoundYield 76%

Procedure

A mixture of 2-chloro-4-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-6-quinazolinemethanol (0.0040 mol), described in International Patent Specification WO 00/39082, in hydrazine (20 ml) and dioxane (40 ml) was stirred at 70° C. for 20 minutes. Saturated sodium chloride solution was added. The mixture was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated till dryness. The residue (2.15 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH; 95/5 to 90/10; 70–200 μm). The pure fractions were collected and the solvent was evaporated, yielding 1.5 g (76%) of 4-(3-chlorophenyl)-α-(4-chlorophenyl)-2-hydrazino-α-(1-methyl-1H-imidazol-5-yl)-6-quinazolinemethanol, mp.186° C. (intermediate 11).

Workup

  1. extractionThe mixture was extracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue (2.15 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH; 95/5 to 90/10; 70–200 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-002dc74ad44549d1873b60f909951546
Source dataset
uspto-grants-2006_05
Patent number
US07053105B2

Reaction notes

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