HCID 86708683, compound → HCID 86708682, compound

HRID 921787Notes

Reaction equation

HRID 921787 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:20][O:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:21]([O-])=O>CO.[Pd]>[NH2:21][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:18][O:19][CH2:20]3)[CH2:13][CH2:12]2)[C:2]=1[Cl:1])[C:6]#[N:7]

Participants

4

Reactant 1

HCID 86708683HCID 86708683, compound

Product 1

HCID 86708682HCID 86708682, compoundYield 12.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-3-nitro-5-((1-(oxetan-3-yl)piperidin-4-yl)oxy)benzonitrile (430 mg, 1.272 mmol) and Pd/C (271 mg, 0.127 mmol) in methanol (20 mL) was hydrogenated at 20 PSI for 1.5 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g gold column, eluting with 1-5% 2 N ammonia in methanol/dichloromethane). 3-amino-4-chloro-5-((1-(oxetan-3-yl)piperidin-4-yl)oxy)benzonitrile (50 mg) was obtained as a foaming solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (40 g gold column, eluting with 1-5% 2 N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-adb5ff4f2c0c4824babb99396d8fa126
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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