1,4-Dioxane → 1-(4-Chloro-3-trifluoromethylphenyl)-3-[2-(6,7-dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]urea

HRID 2108920Notes

Reaction equation

HRID 2108920 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[S:18][C:19]2[CH:25]=[C:24]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([C:37]([F:40])([F:39])[F:38])[CH:31]=3)=[O:28])[CH:23]=[CH:22][C:20]=2[N:21]=1.O1CCOCC1>CN(C)C=O>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:27]([NH:26][C:24]2[CH:23]=[CH:22][C:20]3[N:21]=[C:17]([NH:16][C:2]4[C:11]5[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=5)[N:5]=[CH:4][N:3]=4)[S:18][C:19]=3[CH:25]=2)=[O:28])=[CH:31][C:32]=1[C:37]([F:39])([F:38])[F:40]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 231325021-(2-Aminobenzothiazol-6-yl)-3-(4-chloro-3-trifluoromethylphenyl)urea2×

Product 1

HCID 231325001-(4-Chloro-3-trifluoromethylphenyl)-3-[2-(6,7-dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Chloro-3-trifluoromethylphenyl)-3-[2-(6,7-dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]urea was prepared from 4-chloro-6,7-dimethoxyquinazoline (Fluorochem, 29 mg, 0.13 mmol) and 1-(2-aminobenzothiazol-6-yl)-3-(4-chloro-3-trifluoromethylphenyl)urea (Intermediate 3, 50 mg, 0.13 mmol) according to GP 1. Dimethylformamide was used as a solvent instead of dioxane. After removal of the solvent in vacuo, the residue was subjected to silica gel chromatography applying a dichloromethane-methanol gradient. The crude product was dissolved in dimethylformamide (2 mL) and water was added (2 mL). After storage at 4° C. overnight, the resulting precipitate was filtered off, washed with water and dried to obtain a yellow solid (27 mg, 48 μmol, 37%). LC/ESI-MS: m/z=575 [M(35Cl)+H]+; m/z=573 [M(35Cl)−H]=; Rt=4.14 min.

Workup

  1. customAfter removal of the solvent in vacuo
  2. dissolutionThe crude product was dissolved in dimethylformamide (2 mL)
  3. additionwater was added (2 mL)
  4. filtrationAfter storage at 4° C. overnight, the resulting precipitate was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-079fe20d19e9460b9796270e134eadc3
Source dataset
uspto-grants-2009_04
Patent number
US07514460B2

Reaction notes

Loading…