Piperidine → HCID 58614790, compound

HRID 923165Notes

Reaction equation

HRID 923165 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][C:26]=1[CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:12]=1)=[O:9].C(N(CC)CC)C.[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.C(N(C(C)C)C(C)C)C>ClCCl.C(#N)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8](=[O:9])[C:7]2[CH:24]=[CH:25][C:26]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])=[C:5]([O:4][CH2:3][CH2:2][N:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)[CH:6]=2)=[CH:12][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 66877367HCID 66877367, compound

Product 1

HCID 58614790HCID 58614790, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-(2-Bromoethoxy)-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonylmethyl)benzamide (50 mg, 0.095 mmol) was dissolved in dichloromethane (1.0 ml), treated with triethylamine (20 μl, 0.15 mmol) and piperidine (11 μl, 0.11 mmol), and stirred 2.0 hours at room temperature. Acetonitrile (0.25 ml) and N-ethyl-N-isopropylpropan-2-amine (25 μl, 0.19 mmol) were added, and the reaction was stirred for an additional 45 hours. The reaction was quenched in water and extracted with dichloromethane twice. The dichloromethane extracts were washed with water once, brine once, dried with MgSO4, and evaporated to an solid which was purified by reverse phase HPLC to yield 17 mg N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonylmethyl)-3-(2-(piperidin-1-yl)ethoxy)benzamide. MS (Q1) 528 (M)+.

Workup

  1. stirringthe reaction was stirred for an additional 45 hours
  2. customThe reaction was quenched in water
  3. extractionextracted with dichloromethane twice
  4. washThe dichloromethane extracts were washed with water once
  5. dry with materialbrine once, dried with MgSO4
  6. customevaporated to an solid which
  7. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-076f36268b2c4e78b79d09f5672ec867
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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