1-(Chloromethoxy)-2-methoxyethane → 1-[3-(2-methoxy-ethoxymethyl)-4-oxo-3,4,6,7,8,9-hexahydro-benzo[g]quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1428856노트

반응식

HRID 1428856 반응식
CCN(C(C)C)C(C)C.[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[NH:29][C:28](=[O:30])[C:27]3[C:22](=[CH:23][C:24]4[CH2:34][CH2:33][CH2:32][CH2:31][C:25]=4[CH:26]=3)[N:21]=2)[CH:19]=1)=[O:14])[CH3:11].C(OC(C1C=NN(C2NC(=O)C3C4CCCCC=4C=CC=3N=2)C=1)=O)C.Cl[CH2:61][O:62][CH2:63][CH2:64][O:65][CH3:66]>C1COCC1.CCOC(C)=O>[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[N:29]([CH2:61][O:62][CH2:63][CH2:64][O:65][CH3:66])[C:28](=[O:30])[C:27]3[C:22](=[CH:23][C:24]4[CH2:34][CH2:33][CH2:32][CH2:31][C:25]=4[CH:26]=3)[N:21]=2)[CH:19]=1)=[O:14])[CH3:11]

참가 물질

7

반응물 4

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 1363371811-(4-oxo-3,4,6,7,8,9-hexahydro-benzo[g]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl esterHCID 1363371821-(1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

생성물 1

HCID 684848471-[3-(2-methoxy-ethoxymethyl)-4-oxo-3,4,6,7,8,9-hexahydro-benzo[g]quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester수율 41%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

DIEA (0.76 mL, 4.4 mmol) was added to a 2:1 mixture of 1-(4-oxo-3,4,6,7,8,9-hexahydro-benzo[g]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester and 1-(1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.500 g, 1.478 mmol) in THF (7.4 mL), followed by 1-chloromethoxy-2-methoxy-ethane (0.186 mL, 1.63 mmol). The reaction mixture was stirred at room temperature for 18 h, diluted with EtOAc (40 mL), and washed with water (30 mL). The aqueous layer was extracted with EtOAc (2×30 mL) and the combined organic layers were washed with brine (40 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (5-60% EtOAc/hexanes) to yield the titled compound (0.257 g, 41% yield) and 1-[2-(2-methoxy-ethoxymethyl)-1-oxo-1,2,7,8,9,10-hexahydro-benzo[t]quinazolin-3-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (69.0 mg, 11% yield).

후처리

  1. washwashed with water (30 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
  3. washthe combined organic layers were washed with brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by FCC (5-60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-92a598e2b034447d9de07f8a71ff93e6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937078B2

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