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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)-2-oxo-ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 529856
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HRID 529856 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH:26]([F:28])[F:27])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][NH:10][N:9]=2)[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:36][C:37]([N:39]1[CH2:48][CH2:47][C:42]2([O:46][CH2:45][CH2:44][O:43]2)[CH2:41][CH2:40]1)=[O:38]>CN(C)C=O.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH:26]([F:28])[F:27])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:36][C:37]([N:39]3[CH2:40][CH2:41][C:42]4([O:46][CH2:45][CH2:44][O:43]4)[CH2:47][CH2:48]3)=[O:38])[N:9]=2)[CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 438316402-Chloro-1-{1,4-dioxa-8-azaspiro[4.5]decan-8-yl}ethan-1-oneHCID 178522413HCID 178522413, 화합물

생성물 1

HCID 118523245N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)-2-oxo-ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 76.3%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
2회
HCID 6344Dichloromethane용매

실험 절차

To N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (4.65 g, 11.5 mmol) and cesium carbonate (10.08 g, 30.94 mmol) was added N,N-Dimethylformamide (40 mL) and stirred at room temperature for 5 minutes. To this was added 2-Chloro-1-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)ethan-1-one (5.34 g, 20.2 mmol) in N,N-Dimethylformamide (4.5 mL) and stirred at room temperature for 3 and a half hours. LC/MS (method 31) shows reaction complete. The reaction was then filtered and the filtrate was concentrated under reduced pressure to give a red oil. This was then dissolved in 30 mL dichloromethane and purified by ISCO using a silica column and eluting with 0-100% Ethyl acetate in heptane in 5 minutes followed by 0-15% Methanol in dichloromethane to give 5.16 g (8.78 mmol) of N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)-2-oxo-ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide as a yellow foamy solid. LC/MS (method 39) [M+H]+=589.2, RT=1.91 min.

후처리

  1. stirringstirred at room temperature for 3 and a half hours
  2. customreaction complete
  3. filtrationThe reaction was then filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give a red oil
  6. custompurified by ISCO
  7. washeluting with 0-100% Ethyl acetate in heptane in 5 minutes

출처 및 근거

ORD 기록
ord-8ae98a742efd4d5ea5085311c303520b
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346815B2

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