Sodium bis(trimethylsilyl)amide → HCID 18929588, compound

HRID 1599092Notes

Reaction equation

HRID 1599092 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[C:4](=[O:34])[CH2:3]1.C[Si]([N-:39][Si](C)(C)C)(C)C.[Na+].C1(P(C2C=CC=CC=2)(ON)=O)C=CC=CC=1>CN(C=O)C.C1COCC1>[NH2:39][CH:3]1[C:2](=[O:1])[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:11])[CH:7]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:6]2[N:5]([C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)[C:4]1=[O:34]

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 67575630HCID 67575630, compound

Product 1

HCID 18929588HCID 18929588, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 80 mg (0.175 mmol) 2-(2,4-Dioxo-5-pyridin-4-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl )-acetamide in 3 mL DMF was added 0.210 mL (0.209 mmol, 1.2 equiv) 1N Sodium bis(trimethylsilyl)amide in THF at 0° C. After stirring 0.5 h, 62 mg (0.262 mmol; 1.5 equiv) O-(diphenyl-phosphinyl)hydroxylamine (Harger, J. C. S. Perkin I, 3284-3288 (1981)) was added and the reaction mixture stirred 16 h at ambient temperature. The reaction mixture was filtered and the filtrate concentrated in vacuo. The crude product was purified by flash chromatography on 5 g silica gel eluted successively with EtOAc (100 mL), DCM/CH3OH (19:1, 100 mL). Appropriate fractions were combined and concentrated in vacuo to give the title compound as a clear glass: low resolution MS (FAB) m/z 474.2 (MH+); TLC Rf=0.31 (DCM/CH3OH, 19:1)).

Workup

  1. stirringthe reaction mixture stirred 16 h at ambient temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude product was purified by flash chromatography on 5 g silica gel
  5. washeluted successively with EtOAc (100 mL), DCM/CH3OH (19:1, 100 mL)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aed21ee495104a02b0c1988fe6b29bdc
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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