Dimethylformamide → HCID 59681813, compound

HRID 1394179Notes

Reaction equation

HRID 1394179 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2(C3C=CC(NCCN(C)C)=CC=3)[NH:15][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:9]=3[NH:8]2)=[N:4][O:5][N:6]=1.[H-].[Na+].Cl.C[N:32]([CH3:36])[CH2:33][CH2:34]Cl.[CH3:37][N:38]([CH:40]=O)[CH3:39]>>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:9]3[CH:10]=[CH:11][C:33]([NH:32][CH2:36][CH2:40][N:38]([CH3:39])[CH3:37])=[CH:34][CH:14]=3)[C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:15]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 69197427HCID 69197427, compound

Product 1

HCID 59681813HCID 59681813, compoundYield 4%

Conditions

Temperature
60 °C

Procedure

To a solution containing 500 mg the product from Step 1 (1.7 mmol) in 10 mL DMF was added 200 mg of NaH (60% dispension in oil, 5.1 mmol). After 2 hours at room temperature, 246 mg of 2-(dimethylamino)ethyl chloride hydrochloride (1.7 mmol) was added, and the reaction mixture was heated to 60° C. for 5 hours. The solvent was evaporated in vacuo to yield a residue which was partitioned between ethyl acetate and brine. The organic phase was dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. Purification of the residue by Gilson reverse-phase HPLC afforded the title compound (24 mg, 4%). MS (ES+) m/e 365 [M+H]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto yield a residue which
  3. customwas partitioned between ethyl acetate and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by Gilson reverse-phase HPLC

Sources & evidence

ORD record
ord-0ed5b5476ae54a32a89347e8a107386d
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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