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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cyclopropanecarbonyl chloride → 2-chloro-3-(1-cyanocyclopropyl)-N-(cyclopropylcarbonyl)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-2-fluorophenyl]benzamide

HRID 1800662
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HRID 1800662 반응식
[Cl:1][C:2]1[C:33]([C:34]2([C:37]#[N:38])[CH2:36][CH2:35]2)=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[N:19]=[C:18]3[S:20][C:21]([NH:23][C:24]([CH:26]4[CH2:28][CH2:27]4)=[O:25])=[N:22][C:17]3=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:8]=1[F:29])=[O:5].[CH:39]1([C:42](Cl)=[O:43])[CH2:41][CH2:40]1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:33]([C:34]2([C:37]#[N:38])[CH2:36][CH2:35]2)=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([N:6]([C:42]([CH:39]1[CH2:41][CH2:40]1)=[O:43])[C:7]1[CH:12]=[C:11]([O:13][C:14]2[N:19]=[C:18]3[S:20][C:21]([NH:23][C:24]([CH:26]4[CH2:28][CH2:27]4)=[O:25])=[N:22][C:17]3=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:8]=1[F:29])=[O:5]
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참가 물질

5

반응물 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 252061852-Chloro-3-(1-Cyanocyclopropyl)-N-[5-({2-[(Cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-B]pyridin-5-Yl}oxy)-2-Fluorophenyl]benzamide

생성물 1

HCID 452553512-chloro-3-(1-cyanocyclopropyl)-N-(cyclopropylcarbonyl)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-2-fluorophenyl]benzamide수율 63%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 1049Pyridine용매

실험 절차

To a solution of 2-chloro-3-(1-cyanocyclopropyl)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-2-fluorophenyl]benzamide (3.5 g, 6.39 mmol) produced in Example C127(x) in pyridine (35 mL) were added N,N-dimethylpyridine-4-amine (3.87 g, 31.7 mmol) and cyclopropanecarbonyl chloride (3.0 mL, 33.1 mmol) at 10° C., and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was poured into ice water (70 mL), and the mixture was extracted with ethyl acetate (80 mL×3). The organic layers were combined, washed successively with water (50 mL) and saturated brine (30 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→20/80). The obtained residue was recrystallized from ethyl acetate to give the title compound (2.47 g, 63%) as white crystals.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (80 mL×3)
  2. washwashed successively with water (50 mL) and saturated brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→20/80)
  6. customThe obtained residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-fd9628f4ab434843a0f5ba418692f379
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08344135B2

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