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Cesium fluoride → (s)-3-(2,6-Dimethyl-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenoxy)-propane-1,2-diol

HRID 1177570
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HRID 1177570 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:19][CH2:18]2)[N:11]=3)[CH:5]=[C:4]([CH3:26])[C:3]=1[OH:27].[F-].[Cs+].[CH2:30]1[O:32][C@H:31]1[CH2:33][OH:34]>CN(C=O)C>[CH3:26][C:4]1[CH:5]=[C:6]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:18][CH2:19]2)[N:11]=3)[CH:7]=[C:2]([CH3:1])[C:3]=1[O:27][CH2:30][C@@H:31]([OH:32])[CH2:33][OH:34]
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5

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HCID 25953Cesium fluorideHCID 6973630(-)-GlycidolHCID 1363975962,6-Dimethyl-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenol

생성물 1

HCID 44599850(s)-3-(2,6-Dimethyl-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenoxy)-propane-1,2-diol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of 2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenol (36.7 mg, 99 μmol) and cesium fluoride (1.5 mg, 9.9 μmol) in anhydrous DMF (0.5 mL) was stirred at 25° C. for 1 h. (S)-(−)-glycidol (14 μl, 207 μmol) was then added, and the resulting mixture was heated under argon at 80° C. for 7 d. The reaction mixture was subsequently cooled to 25° C., filtered through Celite, diluted with DMSO (1.5 mL), and purified by rpHPLC (10-100% CH3CN/water+0.1% TFA) to provide (S)-3-(2,6-dimethyl-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenoxy)-propane-1,2-diol as a light yellow solid. MS (ESI) m/z: Calculated: 446.2; Observed: 447.2 (M++1).

후처리

  1. additionwas then added
  2. temperatureThe reaction mixture was subsequently cooled to 25° C.
  3. filtrationfiltered through Celite
  4. additiondiluted with DMSO (1.5 mL)
  5. custompurified by rpHPLC (10-100% CH3CN/water+0.1% TFA)

출처 및 근거

ORD 기록
ord-96437959ac174a9488855ed113faae6e
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842685B2

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