Sodium bis(trimethylsilyl)amide → HCID 59435963, compound

HRID 1802465Notes

Reaction equation

HRID 1802465 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7](Cl)[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3.[NH2:18][C:19]1[C:24]([Cl:25])=[CH:23][C:22]([S:26]([NH:29][CH2:30][C:31]2[N:32]([CH3:36])[CH:33]=[CH:34][N:35]=2)(=[O:28])=[O:27])=[CH:21][C:20]=1[Cl:37].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22]([S:26]([NH:29][CH2:30][C:31]4[N:32]([CH3:36])[CH:33]=[CH:34][N:35]=4)(=[O:27])=[O:28])=[CH:21][C:20]=3[Cl:37])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 59436058HCID 59436058, compoundHCID 59436075HCID 59436075, compound

Product 1

HCID 59435963HCID 59435963, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 9-bromo-1,5-dichlorobenzo[c]-2,6-naphthyridine (100 mg, 0.31 mmol) (Example 1, Step 5) and 4-amino-3,5-dichloro-N-[(1-methyl-1H-imidazol-2-yl)methyl]benzenesulfonamide (123 mg, 0.37 mmol) in DMA (1.2 mL) was added NaHMDS (0.7 mL, 1 M in THF, 0.7 mmol). The reaction was stirred at room temperature for ten minutes and then heated in the microwave to 100° C. for 15 minutes. The reaction was then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification of the residue by silica gel column chromatography (0-10% MeOH/DCM) afforded the title compound.

Workup

  1. temperatureheated in the microwave to 100° C. for 15 minutes
  2. customThe reaction was then quenched by the addition of sat. aq. NaHCO3 solution
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-60c86f2f16cc4751a1732eb8d7bb6660
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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