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Methanol → Methyl 1-((3-fluoro-4-(5-(1-phenylcyclopentyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate

HRID 1177429
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HRID 1177429 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH2:28][N:29]2[CH2:32][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:30]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH:20]=[CH:19][CH2:18]1)[N:11]=2.O.CO>[Pd].C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:28][N:29]2[CH2:30][CH:31]([C:33]([O:35][CH3:36])=[O:34])[CH2:32]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]1)[N:11]=2
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참가 물질

6

반응물 3

HCID 887MethanolHCID 962WaterHCID 67111616Methyl 1-((3-fluoro-4-(5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)azetidine-3-carboxylate

생성물 1

HCID 67111568Methyl 1-((3-fluoro-4-(5-(1-phenylcyclopentyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of methyl 1-((3-fluoro-4-(5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate (0.333 g, 0.667 mmol) and 10% Pd/C, 50% water (0.355 g, 0.333 mmol) under nitrogen was added 5 mL MeOH and 5 mL THF. The resulting mixture was stirred rapidly under an H2 balloon for 4 h. The reaction mixture was flushed with nitrogen, filtered, rinsing with DCM, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography, ISCO 0-100% EA/hexanes, to give methyl 1-((3-fluoro-4-(5-(1-phenylcyclopentyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate as a clear and colorless oil. MS (ESI) m/z: Calculated: 501.2; Observed: 502.1 (M++1).

후처리

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationfiltered
  3. washrinsing with DCM
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was purified by silica gel chromatography, ISCO 0-100% EA/hexanes

출처 및 근거

ORD 기록
ord-b8487c2686874184ab08f78c6b2e81a2
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842685B2

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