Sodium bis(trimethylsilyl)amide → HCID 178510029, compound

HRID 1919693Notes

Reaction equation

HRID 1919693 reaction equation
N[C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[Si]([N-:15][Si](C)(C)C)(C)C.[Na+].Cl[C:22]1[C:31]2[C:26](=[CH:27][N:28]=[CH:29][CH:30]=2)[C:25]2[CH:32]=[CH:33][CH:34]=[C:35]([C:36]3[NH:40][CH:39]=[N:38][N:37]=3)[C:24]=2[N:23]=1>CN1C(=O)CCC1.Cl>[N:38]1[N:37]=[C:36]([C:35]2[C:24]3[N:23]=[C:22]([NH:15][C:8]4[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[CH:2][C:9]=4[Cl:10])[C:31]4[C:26]([C:25]=3[CH:32]=[CH:33][CH:34]=2)=[CH:27][N:28]=[CH:29][CH:30]=4)[NH:40][CH:39]=1

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 126273632-Amino-3-chlorobenzonitrileHCID 178478306HCID 178478306, compound

Product 1

HCID 178510029HCID 178510029, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
80 °C

Procedure

4 amino-3-chlorobenzonitrile was charged in a vial. NaHMDS (1 M solution in THF, 0.2 ml) was added and the solution stirred at 80° C. for 5 min. A suspension of 5-chloro-7-(4H-1,2,4-triazol-3-yl)benzo[c][2,6]naphthyridine (30 mg) in NMP (0.5 ml) was added and the solution stirred at 80° C. for 30 min. The mixture was cooled down, a few drops of HCl and NMP (1 ml) were added and mixture was purified by preparative HPLC to provide 4-(7-(4H-1,2,4-triazol-3-yl)benzo[c][2,6]naphthyridin-5-ylamino)-3-chlorobenzonitrile (25 mg).

Workup

  1. additionwas added
  2. stirringthe solution stirred at 80° C. for 30 min
  3. temperatureThe mixture was cooled down
  4. custommixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-0f60d9be6ecd43c1b1ef2fc3a24128d6
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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