Sodium bis(trimethylsilyl)amide → HCID 86643797, compound

HRID 1802464Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH3:20])=[CH:4][C:5]([CH3:19])=[C:6]([S:8]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)(=[O:10])=[O:9])[CH:7]=1.[Cl:21][C:22]1[N:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[C:24]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:25]=1N=[C:27]2Cl.[CH3:38][Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[Cl:21][C:22]1[C:23]2[C:28](=[C:27]([NH:1][C:2]3[C:3]([CH3:20])=[CH:4][C:5]([CH3:19])=[C:6]([S:8]([NH:11][CH2:12][C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)(=[O:10])=[O:9])[CH:7]=3)[CH:38]=[C:25]3[CH:33]=[CH:34][C:35]([F:37])=[CH:36][C:24]3=2)[CH:29]=[CH:30][N:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-amino-2,4-dimethyl-N-(pyridin-3-ylmethyl)benzenesulfonamide (300 mg, 1.0 mmol) and 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthyridine (Example 1, Step 5) (250 mg, 0.94 mmol) in THF (4.7 mL) at 0° C. was added NaHMDS (2.8 mL, 1 M in THF, 2.8 mmol). The deep red solution was stirred at 0° C. for ten minutes and then quenched by the addition of sat. aq. NaHCO3 solution. The reaction was extracted with EtOAc and the organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-5% MeOH/DCM) afforded the title compound.

Workup

customquenched by the addition of sat. aq. NaHCO3 solution
extractionThe reaction was extracted with EtOAc
dry with materialthe organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customPurification by silica gel column chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record: ord-66a33a7017534fcc9272b5d154e2ace6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

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