Chloroacetyl chloride → 4-{3-[5-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-imidazo[1,2-a]quinolin-8-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

HRID 2075677노트

반응식

HRID 2075677 반응식
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([S:19][C:20]3[CH:21]=[C:22]([C:26]4([C:32]#[N:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:23]=[CH:24][CH:25]=3)=[CH:7][CH:8]=2)[N:3]=1.CCN(C(C)C)C(C)C.Cl[CH2:44][C:45](Cl)=[O:46]>C(Cl)Cl.O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:9]3[C:4](=[CH:5][C:6]([S:19][C:20]4[CH:21]=[C:22]([C:26]5([C:32]#[N:33])[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)[CH:23]=[CH:24][CH:25]=4)=[CH:7][CH:8]=3)[N:3]3[CH2:44][C:45](=[O:46])[N:1]=[C:2]3[CH:11]=2)=[CH:13][CH:14]=1

참가 물질

6

반응물 3

HCID 6577Chloroacetyl chlorideHCID 81531Diisopropylethylamine2회HCID 670907114-{3-[2-Amino-4-(4-fluoro-phenyl)-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

생성물 1

HCID 670908734-{3-[5-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-imidazo[1,2-a]quinolin-8-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To 3e (120 mg, 0.26 mmol) in CH2Cl2 (3 mL) was added iPr2NEt (0.12 mL, 0.66 mmol), followed by chloroacetyl chloride (0.03 mL, 0.40 mmol), and the reaction was stirred at room temperature. Once complete, the reaction was diluted with water, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was dissolved in C2H4Cl2. iPr2NEt (0.12 mL, 0.66 mol) was added, and the reaction was sealed and heated to 80° C. overnight. After cooling to room temperature, the reaction was concentrated and purified by preparative HPLC to give the desired product.

후처리

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionthe residue was dissolved in C2H4Cl2
  6. customthe reaction was sealed
  7. temperatureheated to 80° C. overnight
  8. temperatureAfter cooling to room temperature
  9. concentrationthe reaction was concentrated
  10. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-98547a335f3442c7aed14bf728517f3d
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919621B2

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