Sodium bis(trimethylsilyl)amide → HCID 58266671, compound

HRID 1888504Notes

Reaction equation

HRID 1888504 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:11][C:12]1[N:17]=[CH:16][C:15]([NH2:18])=[C:14]([C:19]2[C:20](F)=[N:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:27][CH:26]=3)[CH:24]=2)[C:13]=1[CH:39]=[CH2:40]>C1COCC1.[Cl-].[Na+].O.C(OCC)(=O)C>[Cl:11][C:12]1[N:17]=[CH:16][C:15]2[NH:18][C:20]3[N:21]=[CH:22][C:23]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][N:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:27][CH:26]=4)=[CH:24][C:19]=3[C:14]=2[C:13]=1[CH:39]=[CH2:40]

Participants

6

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 58266301HCID 58266301, compound

Product 1

HCID 58266671HCID 58266671, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium bis(trimethylsilyl)amide (1.3 mL, 1.3 mmol) was added to a solution of 6′-chloro-2-fluoro-5-(4-piperidin-1-ylmethyl-phenyl)-5′-vinyl-[3,4′]bipyridinyl-3′-ylamine (53 mg, 0.13 mmol) in anhydrous THF (1 mL) and the resultant solution stirred at ambient temperature for 20 min. The reaction mixture was diluted with brine (5 mL) and ethyl acetate (5 mL). The resultant precipitate was collected by filtration to afford the title compound as a beige powder (13 mg, 26%). 1H NMR (CDCl3, 400 MHz): 8.85 (d, J=2.0 Hz, 1H), 8.77 (d, J=2.0 Hz, 1H), 8.61 (s, 1H), 7.58-7.55 (m, 2H), 7.46 (d, J=8.0 Hz, 2H), 7.22-7.14 (m, 1H), 6.03-6.01 (m, 1H), 5.99-5.97 (m, 1H), 3.56 (s, 2H), 2.47-2.37 (m, 4H), 1.64-1.59 (m, 4H), 1.52-1.44 (m, 2H). LCMS (Method A): RT=6.81 min, M+H+=403/405.

Workup

  1. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-2868edabeda54f2c8f5958557025874a
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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