Sodium hydride → HCID 66919042, compound

HRID 2354187Notes

Reaction equation

HRID 2354187 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([NH:13][C:14](=[O:25])[C:15]3[CH:20]=[C:19](F)[CH:18]=[CH:17][C:16]=3[N+:22]([O-:24])=[O:23])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[OH:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([NH:13][C:14]([C:15]3[CH:20]=[C:19]([CH:18]=[CH:17][C:16]=3[N+:22]([O-:24])=[O:23])[O:27][CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]3)=[O:25])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 669189745-fluoro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitrobenzamide

Product 1

HCID 66919042HCID 66919042, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-fluoro-2-nitrobenzamide (2.0 g) and tert-butyl 4-hydroxy-1-piperidinecarboxylate (1.69 g) in DMF (30 ml) was added sodium hydride (0.896 g of a 60% dispersion in oil) portion-wise (ice bath cooling). The reaction was stirred for 22 hours at room temperature under an atmosphere of argon. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution (200 ml) and the resulting precipitate was collected by filtration, washed with diethyl ether, and air dried to yield tert-butyl 4-{3-[({5-[(cyclopropylamino)carbonyl]-2-methylphenyl}amino)carbonyl]-4-nitrophenoxy}piperidine-1-carboxylate (2.76 g) as a yellow solid; NMR Spectrum: (DMSOd6) 0.60 (m, 2H), 0.70 (m, 2H), 1.40 (s, 9H), 1.60 (m, 2H), 1.97 (m, 2H), 2.30 (s, 3H), 2.84 (m, 1H), 3.23 (m, 2H), 3.66 (m, 2H), 4.88 (m, 1H), 7.29 (m, 2H), 7.31 (s, 1H), 7.60 (d, 1H), 7.95 (s, 1H), 8.17 (d, 1H), 8.38 (d, 1H), 10.10 (s, 1H); Mass Spectrum: M+Na+ 561.

Workup

  1. temperatureportion-wise (ice bath cooling)
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with diethyl ether, and air
  4. customdried

Sources & evidence

ORD record
ord-d6dd805f57ae4d67911d0f93a48aa7b9
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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