HCID 67412477, compound → (s)-5-(2,4-Difluorophenoxy)-1-isobutyl-1h-indazole-6-carboxylic acid (1-hydroxymethyl-3-isopropylaminopropyl)-amide

HRID 2112195Notes

Reaction equation

HRID 2112195 reaction equation
COC1C=CC(C[N:8]([CH:39]([CH3:41])[CH3:40])[CH2:9][CH2:10][C@H:11]([NH:14][C:15]([C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[N:22][N:23]3[CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:19][C:18]=2[O:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[F:38])=[O:16])[CH2:12][OH:13])=CC=1>CO.[Pd]>[OH:13][CH2:12][C@@H:11]([NH:14][C:15]([C:17]1[CH:25]=[C:24]2[C:20]([CH:21]=[N:22][N:23]2[CH2:26][CH:27]([CH3:28])[CH3:29])=[CH:19][C:18]=1[O:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[F:38])=[O:16])[CH2:10][CH2:9][NH:8][CH:39]([CH3:41])[CH3:40]

Participants

4

Reactant 1

HCID 67412477HCID 67412477, compound

Product 1

HCID 67411669(s)-5-(2,4-Difluorophenoxy)-1-isobutyl-1h-indazole-6-carboxylic acid (1-hydroxymethyl-3-isopropylaminopropyl)-amideYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-N-(4-((4-methoxybenzyl)(isopropyl)amino)-1-hydroxybutan-2-yl)-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxamide (0.020 g, 0.033 mmol) in MeOH (5 mL) was added wet Pd/C (0.020 g, 10% by weight). The mixture was purged with hydrogen several times and then stirred at room temperature under H2 atmosphere for 5 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was chromatographed eluting with 10% MeOH in dichloromethane with 2% triethylamine to provide 9.4 mg colorless gel (60% yield). MS (ESI+) m/z 475 (M+1) detected; 1H NMR (400 mHz, CDCl3) δ 8.40 (d, 1H), 8.31 (s, 1H), 7.87 (s, 1H), 7.13 (m, 1H), 7.03 (s, 1H), 7.01 (m, 1H), 6.91 (m, 1H), 4.33 (m, 1H), 4.22 (d, 2H), 3.69 (m, 2H), 2.69 (m, 2H), 2.37 (m, 2H), 1.32 (m, 2H), 1.09 (d, 3H), 1.01 (d, 3H), 0.93 (d, 6H).

Workup

  1. customThe mixture was purged with hydrogen several times
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was chromatographed
  5. washeluting with 10% MeOH in dichloromethane with 2% triethylamine

Sources & evidence

ORD record
ord-c0b6f7f8a3fe45d9930d0c99ef41a7af
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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