Cesium carbonate → HCID 67469660, 화합물

HRID 1522607

반응식

HRID 1522607 반응식
[I:1][C:2]1[C:3]2[C:4](=[CH:8][NH:9][N:10]=2)[N:5]=[CH:6][CH:7]=1.Cl[CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O.C(#N)C.O>[CH3:18][C:15]1([CH3:19])[O:14][C@@H:13]([CH2:12][N:9]2[CH:8]=[C:4]3[N:5]=[CH:6][CH:7]=[C:2]([I:1])[C:3]3=[N:10]2)[CH2:17][O:16]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 178506553HCID 178506553, 화합물

생성물 1

HCID 67469660HCID 67469660, 화합물수율 34.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 18373917Acetonitrile--water (1/1)용매

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온도
120 °C

실험 절차

7-Iodo-2H-pyrazolo[4,3-b]pyridine (100 mg, 0.408 mmol), (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (0.056 ml, 0.408 mmol) and cesium carbonate (266 mg, 0.816 mmol) were combined in DMF (5 mL) at room temperature. The mixture was heated at 120° C. for 1 hour, then cooled and purified by preparative HPLC using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-70% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water to give (S)-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-7-iodo-2H-pyrazolo[4,3-b]pyridine (51 mg, 34.8% yield). MP 85-87° C. MS [M+H] found 360.1.

후처리

  1. temperaturecooled
  2. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-e2f63fd7ee0d4a1598849b8413c228fe
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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