2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide → 2-(4-hydroxy-phenyl)-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide

HRID 1790091Notes

Reaction equation

HRID 1790091 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH:21]=[N:22][N:23]3[CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH:21]=[N:22][N:23]3[CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 114196662-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide

Product 1

HCID 220365922-(4-hydroxy-phenyl)-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Benzyloxy-phenyl)-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide (Example 3, 500 mg, 1.10 mmol) and Pd (50 mg, 10% on carbon) were suspended in ethanol (40 mL) and stirred under a hydrogen atmosphere at room temperature for 6 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.62 (m, 4H), 2.45 (m, 4H), 2.87 (t, 2H, J=6.78), 3.65 (s, 2H), 4.47 (t, 2H, J=6.78), 6.72 (m, 2H), 7.16 (m, 2H), 7.25–7.65 (m, 3H), 8.26 (s, 1H), 9.26 (s, 1H), 10.09 (s, 1H); MS (DCI/NH3) m/z 365 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-25a06987aa1b4da39ce701e2c7785851
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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