Potassium Carbonate → 6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1-{[2-(trifluoromethyl)benzyl]oxy}-1H-pyrrolo[3,2-b]pyridine

HRID 1404597노트

반응식

HRID 1404597 반응식
[OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH:15]=3)[CH:9]=2)[CH:4]=[CH:3]1.Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]([F:40])([F:39])[F:38].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH:19]1[CH2:20][CH2:21][CH:16]([N:14]2[CH:15]=[C:11]([C:8]3[CH:9]=[C:10]4[N:2]([O:1][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[C:37]([F:40])([F:39])[F:38])[CH:3]=[CH:4][C:5]4=[N:6][CH:7]=3)[CH:12]=[N:13]2)[CH2:17][CH2:18]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 67458749tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

생성물 1

HCID 462350476-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1-{[2-(trifluoromethyl)benzyl]oxy}-1H-pyrrolo[3,2-b]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (30 mg, 0.078 mmol, 1.0 eq), 1-(bromomethyl)-2-(trifluoromethyl)benzene (0.066 mmol), and K2CO3 (30 mg) in 1.5 ml of DMF were shaken at r.t. for 30 min and then filtered and evaporated. The resulting crude product was dissolved in 1.5 ml of methanol and 0.5 ml of 4.0 M HCl/dioxane was dropped in. The reaction was shaken at room temperature for 0.5-1 h. The solvent was evaporated and the residue was dissolved in 2 ml of DCM. To this solution were added 20 mg of NaHCO3, 10 mg of Na2CO3, and drops of water. After stirred for 10 min, the organic solution was separated and purified with preparation HPLC to give the final product.

후처리

  1. filtrationfiltered
  2. customevaporated
  3. dissolutionThe resulting crude product was dissolved in 1.5 ml of methanol
  4. addition0.5 ml of 4.0 M HCl/dioxane was dropped in
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in 2 ml of DCM
  7. additionTo this solution were added 20 mg of NaHCO3, 10 mg of Na2CO3, and drops of water
  8. stirringAfter stirred for 10 min
  9. customthe organic solution was separated
  10. custompurified with preparation HPLC

출처 및 근거

ORD 기록
ord-7cf10928087e43148d2e0db5591870eb
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912330B2

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