Dichloromethane → Quinazoline hydrochloride

HRID 547231ノート

反応式

HRID 547231 の反応式
N(C(OCC)=O)=NC(OCC)=O.BrC1C=CC(N[C:19]2[C:28]3[C:23](=[CH:24][C:25](O)=[C:26](OC)[CH:27]=3)[N:22]=[CH:21][N:20]=2)=C(F)C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCN(CCOCCO)CC1.C(Cl)[Cl:67]>>[ClH:67].[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[N:20][CH:21]=1

参加物

6

反応物 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4584644-(2-(2-Hydroxyethoxy)ethyl)morpholineHCID 1355038524-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinol

生成物 1

HCID 21186983Quinazoline hydrochloride収率 49%

実験手順

Diethyl azodicarboxylate (378 μl, 2.4 mmol) was added dropwise to a mixture of 4-(4-bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (292 mg, 0.8 mmol), (prepared as described for the starting material in Example 48), triphenylphosphine (629 mg, 2.4 mmol) and 2-(2-morpholinoethoxy)ethanol (196 mg, 1.12 mmol), (prepared as described for the starting material in Example 53), in methylene chloride (10 ml) under nitrogen. The mixture was stirred for 3.5 hours at ambient temperature and the mixture was purified by pouring it directly on to a column of silica and eluting with methylene chloride/acetonitrile/methanol 6/3/1). The purified product was dissolved in methylene chloride/methanol and the insolubles were removed by filtration. 2M Ethereal hydrogen chloride (1 ml) was added to the filtrate and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(2-morpholinoethoxy)ethoxy)quinazoline hydrochloride (232 mg, 49%).

後処理

  1. custom(prepared
  2. custom(prepared
  3. customthe mixture was purified
  4. additionby pouring it directly on to a column of silica
  5. washeluting with methylene chloride/acetonitrile/methanol 6/3/1)
  6. dissolutionThe purified product was dissolved in methylene chloride/methanol
  7. customthe insolubles were removed by filtration
  8. addition2M Ethereal hydrogen chloride (1 ml) was added to the filtrate
  9. customthe volatiles were removed by evaporation
  10. customThe residue was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried under vacuum

出典と根拠

ORDレコード
ord-deff611cc80349748ca3a0247ac8e75a
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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