Dimethylcarbamoyl Chloride → Quinazoline hydrochloride

HRID 547218ノート

反応式

HRID 547218 の反応式
CN(C)C([Cl:5])=O.ClC1C=CC(N[C:13]2[C:22]3[C:17](=[CH:18][C:19](OCCNC)=[C:20](OC)[CH:21]=3)[N:16]=[CH:15][N:14]=2)=C(F)C=1.C(N(CC)CC)C>C(Cl)Cl>[ClH:5].[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[N:14][CH:15]=1

参加物

5

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 224781924-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(2-methylaminoethoxy)quinazoline

生成物 1

HCID 21186983Quinazoline hydrochloride収率 120%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dimethylcarbamyl chloride (38 μl, 0.42 mmol) was added to a solution of 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methylaminoethoxy)quinazoline (150 mg, 0.4 mmol), (prepared as described for the starting material in Example 60), and triethylamine (61 μl, 0.44 mmol) in methylene chloride (4 ml). The mixture was stirred for 2.5 hours at ambient temperature, the resulting precipitate was collected by filtration and washed with ether. The solid was purified by column chromatography, eluting with methylene chloride/methanol (92/8). The purified product was dissolved in methylene chloride/methanol (1/1), 2.9M ethereal hydrogen chloride (1 ml) was added and the volatiles were removed by evaporation. The residue was triturated with ether and the solid product collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-N′,N′,N′-trimethylureido)ethoxy)quinazoline hydrochloride (80 mg, 41%).

後処理

  1. custom(prepared
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with ether
  4. customThe solid was purified by column chromatography
  5. washeluting with methylene chloride/methanol (92/8)
  6. dissolutionThe purified product was dissolved in methylene chloride/methanol (1/1)
  7. addition2.9M ethereal hydrogen chloride (1 ml) was added
  8. customthe volatiles were removed by evaporation
  9. customThe residue was triturated with ether
  10. filtrationthe solid product collected by filtration
  11. washwashed with ether
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-5331161d8ba8468b946a531d00ef3863
出典データセット
uspto-grants-2011_05
特許番号
USRE042353E1

反応ノート

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