Cesium carbonate → HCID 11683683, 화합물

HRID 917429노트

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HRID 917429 반응식
Br[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:11]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:12][CH:13]=[C:14]([O:17][CH3:18])[C:15]=2[N:16]=1)=[O:6].Cl.[NH:29]1[CH2:32][CH:31]([OH:33])[CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[OH:33][CH:31]1[CH2:32][N:29]([C:2]2[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=2)[C:5]([NH:7][C:8]2[S:9][C:10]3[C:11]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:12][CH:13]=[C:14]([O:17][CH3:18])[C:15]=3[N:16]=2)=[O:6])[CH2:30]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 865972552-bromo-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)isonicotinamide

생성물 1

HCID 11683683HCID 11683683, 화합물수율 15%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
150 °C

실험 절차

A stirred suspension of 200 mg (0.44 mmol) 2-bromo-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide, 487 mg (4.44 mmol) azetidin-3-ol hydrochloride and 2.17 g (6.66 mmol) cesium carbonate in 6 ml N-methyl-pyrrolidone in a thick-walled glass pressure tube fitted with a teflon cap was heated at 150° C. for 6 h. The reaction mixture was then cooled to room temperature and partitioned between ethyl acetate and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. Flash chromatography (methanol/dichloromethane) followed by trituration in ether afforded 29 mg (15%) 2-(3-hydroxy-azetidin-1-yl)-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide as a brown crystalline solid. ES-MS m/e (%): 443 (M+H+, 100).

후처리

  1. customcap
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. custompartitioned between ethyl acetate and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ab8c1961913547e0852ab892348b0ac1
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273865B2

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