1,4-Dioxane → HCID 23132499, compound

HRID 2108922Notes

Reaction equation

HRID 2108922 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]=[CH:24][C:23]([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: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:23]2[CH:24]=[CH:25][C:19]3[S:18][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)=[N:21][C:20]=3[CH:22]=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 23132498HCID 23132498, compound2×

Product 1

HCID 23132499HCID 23132499, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Chloro-3-trifluoromethylphenyl)-3-[2-(6,7-dimethoxyquinazolin-4-ylamino)benzothiazol-5-yl]urea was prepared from 4-chloro-6,7-dimethoxyquinazoline (Fluorochem, 29 mg, 0.13 mmol) and 1-(2-aminobenzothiazol-5-yl)-3-(4-chloro-3-trifluoromethylphenyl)urea (Intermediate 5, 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 storing in the fridge overnight, the resulting precipitate was filtered off, washed with water and dried (yellow solid, 7 mg, 12 μmol, 9%). LC/ESI-MS: m/z=575 [M(35Cl)+H]+; m/z=573 [M(35Cl)−H]−; Rt=4.17 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. customAfter storing in the fridge overnight
  5. filtrationthe resulting precipitate was filtered off
  6. washwashed with water
  7. customdried (yellow solid, 7 mg, 12 μmol, 9%)

Sources & evidence

ORD record
ord-dcb4fc457ae04ec08ac9eabc846969f5
Source dataset
uspto-grants-2009_04
Patent number
US07514460B2

Reaction notes

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