1,4'-Bipiperidine → HCID 59424297, compound

HRID 501970Notes

Reaction equation

HRID 501970 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[C:8]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C@H:22]([CH2:26][C:27]3[CH:35]=[C:34]([CH3:36])[C:33]4[C:29](=[CH:30][N:31]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[N:32]=4)[CH:28]=3)[C:23](O)=[O:24])=[O:20])[CH2:15][CH2:14]1)=[CH:7]2.C(N(CC)C(C)C)(C)C.[N:54]1([CH:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[C:8]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C@H:22]([CH2:26][C:27]3[CH:35]=[C:34]([CH3:36])[C:33]4[C:29](=[CH:30][N:31]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:43])([CH3:42])[CH3:44])[N:32]=4)[CH:28]=3)[C:23](=[O:24])[N:63]3[CH2:64][CH2:65][CH:60]([N:54]4[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]4)[CH2:61][CH2:62]3)=[O:20])[CH2:17][CH2:18]1)=[CH:7]2

Participants

5

Reactant 3

HCID 786071,4'-BipiperidineHCID 81531DiisopropylethylamineHCID 59424353HCID 59424353, compound

Product 1

HCID 59424297HCID 59424297, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-2-(4-(8-Fluoro-2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carbonyloxy)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid (105 mg, 0.17 mmol) was dissolved in N,N-dimethylformamide (3 mL). N,N-Diisopropylethylamine (100 μL, 0.57 mmol) was added to the mixture followed by o-benzotriazol-1-yl-N,N,N′-tetramethyluronium tetrafluoroborate (65 mg, 0.20 mmol). The reaction was stirred at room temperature for 5 min. 4-Piperidinopiperidine (41 mg, 0.22 mmol) was added to the mixture. The reaction was stirred at room temperature for 2 h. The mixture was diluted with ethyl acetae (25 mL), washed successively with water (3×), and brine. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The title compound was obtained without further purification as white solid in 96% yield. Mass spec.: 773.3 (MH)+.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 h
  2. additionThe mixture was diluted with ethyl acetae (25 mL)
  3. washwashed successively with water (3×), and brine
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa204a1168d541f5b1a03f42b343bd4f
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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