Triphenylphosphine → HCID 22625075, 화합물

HRID 279661노트

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HRID 279661 반응식
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([OH:31])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:54]1[CH:59]=[CH:58][CH:57]=[C:56]([CH2:60][CH2:61]O)[CH:55]=1>C(Cl)Cl>[ClH:13].[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH2:61][CH2:60][C:56]4[CH:55]=[N:54][CH:59]=[CH:58][CH:57]=4)=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 805153-PyridineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

생성물 1

HCID 22625075HCID 22625075, 화합물수율 133.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethyl azodicarboxylate (236 μl, 1.5 mmol) was added dropwnise to a suspension of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (160 mg, 0.5 mmol), (prepared as described for the starting material in Example 24), triphenylphosphine (393 mg, 1.5 mmol) and 2-(3-pyridyl)ethanol (86 mg, 0.7 mmol), (J.Heterocycl. Chem. 1992, 29, 1663), in methylene chloride (6 ml) and the mixture stirred for 4 hours at ambient temperature. The mixture was poured directly on to a silica column and eluted with methylene chloride/acetonitrile/methanol (60/35/5). The purified solid was dissolved in methylene chloride/methanol and ethereal hydrogen chloride (1.5 ml of a 4.5M solution) was added. The volatiles were removed by evaporation, the solid residue was suspended in ether, collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(3-pyridyl)ethoxy)quinazoline hydrochloride (154 mg, 52%).

후처리

  1. custom(prepared
  2. additionThe mixture was poured directly on to a silica column
  3. washeluted with methylene chloride/acetonitrile/methanol (60/35/5)
  4. dissolutionThe purified solid was dissolved in methylene chloride/methanol
  5. additionethereal hydrogen chloride (1.5 ml of a 4.5M solution) was added
  6. customThe volatiles were removed by evaporation
  7. filtrationcollected by filtration
  8. washwashed with ether
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-3e4fefddf3af469dbfc393722b7518be
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362336B1

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