Cyclobutanecarbonyl chloride → (2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-thiazolo[5,4-b]pyridin-5-yl)(cyclobutyl)methanone

HRID 1177589

반응식

HRID 1177589 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([Sn](C)(C)C)[N:16]=3)=[C:9]([F:26])[CH:8]=1.[CH:27]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28]1>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:31]([CH:27]2[CH2:30][CH2:29][CH2:28]2)=[O:32])[N:16]=3)=[C:9]([F:26])[CH:8]=1

참가 물질

4

반응물 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 591748322-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(trimethylstannyl)thiazolo[5,4-b]pyridine

생성물 1

HCID 67112767(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-thiazolo[5,4-b]pyridin-5-yl)(cyclobutyl)methanone

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(trimethylstannyl)-thiazolo[5,4-b]pyridine (515.5 mg, 1.076 mmol) and cyclobutanecarbonyl chloride (0.147 mL, 1.291 mmol) in toluene (10.0 mL) was stirred under argon at 80° C. for 22 h. The reaction mixture was then concentrated onto silica gel and chromatographically purified (0-50% EtOAc/hexanes) to provide (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-thiazolo[5,4-b]pyridin-5-yl)(cyclobutyl)methanone as an off-white solid. MS (ESI) m/z: Calculated: 398.1; Observed: 398.9 (M++1).

후처리

  1. concentrationThe reaction mixture was then concentrated onto silica gel
  2. customchromatographically purified (0-50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-e2e239353f8b417197406788148c4c0a
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

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