3-{4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo [1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic Acid Methyl Ester → 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl ester

HRID 8269

Reaction equation

HRID 8269 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]=[CH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:19][N:18]4[CH2:28][CH2:29][CH2:30][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:19][N:18]4[CH2:28][CH2:29][CH2:30][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 666794803-{4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo [1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic Acid Methyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 101799083-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic acid methyl ester (0.041 g, 0.1 mmol) in methanol (1 mL) is added 10% Pd/C (0.1 g). The resulting mixture is placed under one atmosphere of hydrogen and: stirred for 18 h. The mixture is filtered and concentrated in vacuo. The residue is chromatographed on SiO2 (2% methanol in dichloromethane) to yield the desired product as a pale yellow solid, 0.035 g (85%).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue is chromatographed on SiO2 (2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b826b0c50ac4412799c09914093745af
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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