Sodium hydride → HCID 11421062, compound

HRID 2377876Notes

Reaction equation

HRID 2377876 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[C:21]=1[N+:37]([O-:39])=[O:38]>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:20]2[C:21]([N+:37]([O-:39])=[O:38])=[C:22]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=3)[N:23]=[CH:24][N:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 218978866-Chloro-N-[4-(methanesulfonyl)phenyl]-5-nitropyrimidin-4-amine

Product 1

HCID 11421062HCID 11421062, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-(2-Hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (1.0 mmol, 230 μL) and sodium hydride (1.0 mmol, 26 mg) were dissolved in dimethyl acetamide (1.0 mL) and stirred for 30 minutes at room temperature. Then, (6-chloro-5-nitro-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine (0.21 mmol, 70 mg) was added. The reaction was stirred at 70° C. for 20 minutes. Its progress was monitored by thin layer chromatography and LCMS. Sodium hydride was quenched with water and the desired compound was extracted in ethyl acetate. Organic solvents were evaporated in vacuo. Flash chromatography (Silica gel 60; 40/60 EtoAc/Hexanes) provided Compound A14 as a yellow oil (90 mg, 82%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.26 (s, 1H), 8.40 (s, 1H), 7.98 (d, 2H), 7.86 (d, 2H), 4.51 (t, 2H), 4.09 (m, 2H), 3.73 (t, 2H), 3.07 (s, 3H), 2.72 (m, 2H), 1.76 (m,1H), 1.55 (q, 2H), 1.46 (s, 9H), 1.15 (m, 2H). LCMS (ESI), m/z 422.2 (M+H+, 100%).

Workup

  1. stirringThe reaction was stirred at 70° C. for 20 minutes
  2. customSodium hydride was quenched with water
  3. extractionthe desired compound was extracted in ethyl acetate
  4. customOrganic solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-af1afb5bc6c14e479538389474b9c150
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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