Cesium carbonate → (R)-1-methyl-6-(4-((1-(pyridin-2-yl)pyrrolidin-3-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517956노트

반응식

HRID 517956 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]#[N:15])[C:11]3[N:16]=[N:17][N:18]([CH3:19])[C:10]=3[CH:9]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].CS(O[CH2:29][C@@H:30]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[CH2:31]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[CH3:19][N:18]1[C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([O:1][CH2:29][C@@H:30]4[CH2:34][CH2:33][N:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=5)[CH2:31]4)=[C:3]([C:20]([F:23])([F:22])[F:21])[CH:4]=3)[N:13]=[C:12]([C:14]#[N:15])[C:11]=2[N:16]=[N:17]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 86673350(R)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methyl methanesulfonateHCID 1363523116-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

생성물 1

HCID 67298160(R)-1-methyl-6-(4-((1-(pyridin-2-yl)pyrrolidin-3-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

6-(4-Hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (0.235 mmol, 0.075 g), (R)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methyl methanesulfonate (0.282 mmol, 0.072 g), cesium carbonate (0.352 mmol, 0.115 g) and tetrabutylammonium iodide (0.117 mmol, 0.043 g) were stirred in DMF (1 ml) at 50° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and dried over Na2SO4. The resulting residue was triturated with ether and filtered. The solid was sonicated in methanol, filtered and dried to afford (R)-1-methyl-6-(4-((1-(pyridin-2-yl)pyrrolidin-3-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile. (47 mg)

후처리

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. customThe resulting residue was triturated with ether
  4. filtrationfiltered
  5. customThe solid was sonicated in methanol
  6. filtrationfiltered
  7. customdried

출처 및 근거

ORD 기록
ord-dcc83e59f33242fb854f399af51c754c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115126B2

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