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

HRID 1404597ノート

反応式

HRID 1404597 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7cf10928087e43148d2e0db5591870eb
出典データセット
uspto-grants-2014_12
特許番号
US08912330B2

反応ノート

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